supporting information - wiley-vch · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 o obz o tbso bno o o np ht...
TRANSCRIPT
![Page 1: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/1.jpg)
Supporting Information
© Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006
![Page 2: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/2.jpg)
1
A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids and Its Application in
Glycosaminoglycan Syntheses
Lijun Huang, Nardos Teumelsan, Xuefei Huang*
Department of Chemistry, The University of Toledo, 2801 W. Bancroft Street, MS 602, Toledo, OH 43606, USA
Corresponding author: Tel: 1-419-530-1507; Fax: 1-419-530-4033;
Email: [email protected]
![Page 3: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/3.jpg)
2
1H- and 13C- NMR Spectra
OH
O
4
1H-NMR (600 MHz, CDCl3)
![Page 4: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/4.jpg)
3
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
![Page 5: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/5.jpg)
4
250 200 150 100 50 0
OH
O
4
13C-NMR (100 MHz, CDCl3)
![Page 6: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/6.jpg)
5
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
OH
O
MeO 6
1H-NMR (600 MHz, CDCl3)
![Page 7: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/7.jpg)
6
OH
O
MeO 6
13C-NMR (100 MHz, CDCl3)
250 200 150 100 50 0
![Page 8: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/8.jpg)
7
![Page 9: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/9.jpg)
8
OH
4O 8
1H-NMR (400 MHz, CDCl3)
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
![Page 10: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/10.jpg)
9
OH
4O 8
13C-NMR (100 MHz, CDCl3)
![Page 11: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/11.jpg)
10
250 200 150 100 50 0
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11
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
OOH
O O
O
O
O
10
1H-NMR (600 MHz, CDCl3)
![Page 13: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/13.jpg)
12
![Page 14: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/14.jpg)
13
250 200 150 100 50 0
OOH
O O
O
O
O
10
13C-NMR (100 MHz, CDCl3)
![Page 15: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/15.jpg)
14
OOH
OBzSTol
BzOBzO
O
12
1H-NMR (400 MHz, CDCl3)
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
![Page 16: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/16.jpg)
15
250 200 150 100 50 0
OOH
OBzSTol
BzOBzO
O
12
13C-NMR (100 MHz, CDCl3)
![Page 17: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/17.jpg)
16
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OOH
NPhthSTol
BnOPMBO
O
14
1H-NMR (400 MHz, CDCl3)
![Page 18: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/18.jpg)
17
OOH
NPhth
STolBnOPMBO
O
14
13C-NMR (100 MHz, CDCl3)
250 200 150 100 50 0
![Page 19: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/19.jpg)
18
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OO
NPhth
BnOPMBO
O
1H-NMR (400 MHz, CDCl3)
15
![Page 20: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/20.jpg)
19
![Page 21: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/21.jpg)
20
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OHO
NPhthSTol
BnOTBSO
17
O
1H-NMR (600 MHz, CDCl3)
![Page 22: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/22.jpg)
21
OHO
NPhthSTol
BnOTBSO
17
O
13C-NMR (150 MHz, CDCl3)
250 200 150 100 50 0
![Page 23: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/23.jpg)
22
OHO OBz
O
BzOBzO
O
19
![Page 24: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/24.jpg)
23
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
![Page 25: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/25.jpg)
24
O
HO OBz
O
BzOBzO
O
19
13C-NMR (100 MHz, CDCl3)
![Page 26: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/26.jpg)
25
250 200 150 100 50 0
![Page 27: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/27.jpg)
26
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
1H-NMR (600 MHz, CDCl3)
OOBn
NPhthOMe
HOBnO
O
21
![Page 28: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/28.jpg)
27
13C-NMR (150 MHz, CDCl3)
OOBn
NPhthOMe
HOBnO
O
21
200 150 100 50 0
![Page 29: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/29.jpg)
28
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29
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
O
NPhth
OMeOBnO
1H-NMR (400 MHz, CDCl3)
BnO O
O
NPhth
OMeHOBnO
O
22
![Page 31: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/31.jpg)
30
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
OHO OMe
O O
O
24
1H-NMR (600 MHz, CDCl3)
![Page 32: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/32.jpg)
31
OHO OMe
O O
O
24
13C-NMR (150 MHz, CDCl3)
![Page 33: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/33.jpg)
32
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
O
OBz
OBnO
BnOO
O
NPhthOMe
OPh
26
HO O
1H-NMR (400 MHz, CDCl3)
![Page 34: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/34.jpg)
33
![Page 35: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/35.jpg)
34
O
OBz
OBnO
BnOO
O
NPhthOMe
OPh
26
HO O
13C-NMR (100 MHz, CDCl3)
![Page 36: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/36.jpg)
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250 200 150 100 50 0
![Page 37: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/37.jpg)
36
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
![Page 38: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/38.jpg)
37
O
OBz
OTBSOBnO
OO
NPhth
OPhO
OBz
OOBnO
OO
NPhth
OMeOPhBnO O BnO O
29
1H-NMR (600 MHz, CD2Cl2)
![Page 39: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/39.jpg)
38
O
OBz
OTBSOBnO
OO
NPhth
OPhO
OBz
OOBnO
OO
NPhth
OMeOPhBnO O BnO O
29
13C-NMR (100 MHz, CD2Cl2)
![Page 40: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/40.jpg)
39
250 200 150 100 50 0
![Page 41: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/41.jpg)
40
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
O
OBz
OTBSOBnO
OO
NPhth
OPhO
OBz
OOBnO
OO
NPhth
OPhBnO O BnO O
30
O
OBz
OOBnO
OO
NPhth
OMeOPh
BnO O
1H-NMR (600 MHz, CD2Cl2)
![Page 42: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/42.jpg)
41
250 200 150 100 50 0
O
OBz
OTBSOBnO
OO
NPhth
OPhO
OBz
OOBnO
OO
NPhth
OPhBnO O BnO O
30
O
OBz
OOBnO
OO
NPhth
OMeOPhBnO O
13C-NMR (100 MHz, CD2Cl2)
![Page 43: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/43.jpg)
42
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43
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
O
OBz
OTBSOBnO
O
O
NPhth
O
O
OBn
OMeO
BnO
Ph
32
BnO O BnO O
1H-NMR (600 MHz, CDCl3)
![Page 45: Supporting Information - Wiley-VCH · 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2 O OBz O TBSO BnO O O NP ht O OBn BnO OMe Ph 32 Bn O BnO O 1H-NMR (600 MHz, CDCl 3) 44. 45 1 O OBz O TBSO BnO](https://reader036.vdocuments.us/reader036/viewer/2022070712/5ecc27258304d125c83be31d/html5/thumbnails/45.jpg)
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O
OBz
OTBSOBnO
O
O
NPhth
O
O
OBn
OMeOBnO
Ph
32
BnO O BnO O
13C-NMR (150 MHz, CDCl3)
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 -20
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12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
O
OBz BnOTBSO
BnO OOBn
N3
O
O
OBnOMeO
BnO34
1H-NMR (600 MHz, CDCl3)
BnO O
BnO O
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170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
O
OBz BnOTBSO
BnO OOBn
N3
O
O
OBnOMeO
BnO34
13C-NMR (150 MHz, CDCl3)
BnO O
BnO O