Supporting Information · 2006-12-27 · OBz S O O 8 Me (100 MHz, CDCl3) 4 13 12 11 10 9 8 7 6 5 4...
Transcript of Supporting Information · 2006-12-27 · OBz S O O 8 Me (100 MHz, CDCl3) 4 13 12 11 10 9 8 7 6 5 4...
![Page 1: Supporting Information · 2006-12-27 · OBz S O O 8 Me (100 MHz, CDCl3) 4 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 O BnO OBz STol OPMB HO 17 (400 MHz, CDCl 3) 5 250 200 150 100 50 0 (100](https://reader034.fdocuments.us/reader034/viewer/2022042301/5ecc08466c348842c3653745/html5/thumbnails/1.jpg)
Supporting Information
© Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006
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1
Highly Efficient Syntheses of Hyaluronic Acid Oligosaccharides
Lijun Huang, Xuefei Huang*
Department of Chemistry
The University of Toledo
2801 W. Bancroft St. MS 602
Toledo, OH 43606 (USA)
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2
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OBnO
OBz
SO
O
8
MeO
(400 MHz, CDCl3)
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3
250 200 150 100 50 0
OBnO
OBz
SO
O
8
MeO
(100 MHz, CDCl3)
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4
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OBnO
OBz
STol
OPMB
HO
17(400 MHz, CDCl3)
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5
250 200 150 100 50 0
(100 MHz, CDCl3)
OBnO
OBz
STol
OPMB
HO
17
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6
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
OBnO
OBz
STol
OPMB
TBSO
11(400 MHz, CDCl3)
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7
250 200 150 100 50 0
OBnO
OBz
STol
OPMB
TBSO
11(100 MHz, CDCl3)
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8
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
(400 MHz, CDCl3)
OBnO
BzO
PMBOTBSO O
ONPhth
STolO
OPh
14β
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9
250 200 150 100 50 0
(100 MHz, CDCl3)
OBnO
BzO
PMBOTBSO O
ONPhth
STolO
OPh
14β
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10
(400 MHz, CDCl3)
OBnO
BzO
PMBOTBSO O
ONPhth
OCH3
OO
Ph
15
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
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11
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
(100 MHz, CDCl3)
OBnO
BzO
PMBOTBSO O
ONPhth
OCH3
OO
Ph
15
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12
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
(400 MHz, CDCl3)
OBnO
BzO
PMBOO
OO
PhthN
OCH3
OO
PhO
BnOBzO
PMBOTBSO
OO
PhthN
OO
Ph
19
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13
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
(100 MHz, CDCl3)
OBnO
BzO
PMBOO
OO
PhthN
OCH3
OO
PhO
BnOBzO
PMBOTBSO
OO
PhthN
OO
Ph
19
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14
11 10 9 8 7 6 5 4 3 2 1 0
(100 MHz, CDCl3)
OBnO
BzO
PMBOHO O
ONPhth
OCH3
OO
Ph
22
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15
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0
(400 MHz, CDCl3)
OBnO
BzO
PMBOHO O
ONPhth
OCH3
OO
Ph
22
(100 MHz, CDCl3)
OBnO
BzO
PMBOHO O
ONPhth
OCH3
OO
Ph
22
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16
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
(400 MHz, CD2Cl2)
OBnO
BzO
PMBOO
OO
PhthN
OCH3
OO
PhOO
PhthN
OO
PhO
BnOBzO
PMBOO
OTBSO
PhthN
OO
Ph
28
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17
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
(100 MHz, CD2Cl2)
OBnO
BzO
PMBOO
OO
PhthN
OCH3
OO
PhOO
PhthN
OO
PhO
BnOBzO
PMBOO
OTBSO
PhthN
OO
Ph
28
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18
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
(600 MHz, CD2Cl2)
OBnO
BzO
PMBOTBSO
OO
PhthN
OO
PhO
BnOBzO
PMBOO O
O
PhthN
OO
PhO
BnOBnO
PMBOO
OCH3
29
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19
250 200 150 100 50 0
(150 MHz, CD2Cl2)
OBnO
BzO
PMBOTBSO
OO
PhthN
OO
PhO
BnOBzO
PMBOO O
O
PhthN
OO
PhO
BnOBnO
PMBOO
OCH3
29
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20
12 11 10 9 8 7 6 5 4 3 2 1 0 -1 -2
(600 MHz, CDCl3)
OBnO
BzO
PMBOO
OO
PhthN
OCH3
OO
PhO
BnOBzO
PMBOO
OO
PhthN
OO
PhO
BnOBzO
PMBOTBSO
OO
PhthN
OO
Ph
30
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21
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
(100 MHz, CDCl3)
OBnO
BzO
PMBOO
OO
PhthN
OCH3
OO
PhO
BnOBzO
PMBOO
OO
PhthN
OO
PhO
BnOBzO
PMBOTBSO
OO
PhthN
OO
Ph
30
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22
13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1
(600 MHz, CDCl3)
OBnO
BzO
HOO
OO
PhthN
OCH3
OO
PhO
BnOBzO
HOO O
OPhthN
OO
PhO
BnOBzO
HOTBSO O
OPhthN
OO
Ph
36
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23
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
(100 MHz, CDCl3)
OBnO
BzO
HOO O
OPhthN
OCH3
OO
PhOBnO
BzO
HOO O
OPhthN
OO
PhO
BnOBzO
HOTBSO O
OPhthN
OO
Ph
36
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24
10.0 9.5 9.0 8.5 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 -1.0
(400 MHz, CD2Cl2)
OBnO
BzO
BnOO
OO
PhthN
OCH3
OO
PhO
BnOBzO
BnOO
OO
PhthN
OO
PhO
BnOBzO
BnOTBSO
OO
PhthN
OO
Ph
37
O O O
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25
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
(100 MHz, CD2Cl2)
OBnO
BzO
BnOO
OO
PhthN
OCH3
OO
PhO
BnOBzO
BnOO
OO
PhthN
OO
PhO
BnOBzO
BnOTBSO
OO
PhthN
OO
Ph
37
O O O
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26
9.0 8.5 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
(400 MHz, D2O)
OHO
HO
HO2CO O
OAcHN
OCH3
HOHOO
HOHO
HO2CO O
OAcHN
HOHO
38
OHO
HO
HO2CHO O
OAcHN
HOHO
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27
200 150 100 50 0
(100 MHz, D2O)
OHO
HO
HO2CO O
OAcHN
OCH3
HOHOO
HOHO
HO2CO O
OAcHN
HOHO
38
OHO
HO
HO2CHO O
OAcHN
HOHO
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28
(600 MHz, D2O)
OHO
HO
HO2CHO O
OAcHN
OCH3
HOHO
39
9.0 8.5 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
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29
9.0 8.5 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 -1.0
(600 MHz, D2O)
OHO
HO
HO2CO O
OAcHN
OCH3
HOHOO
HOHO
HO2CHO O
OAcHN
HOHO
40
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30
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 -20
(100 MHz, D2O)
OHO
HO
HO2CO O
OAcHN
OCH3
HOHOO
HOHO
HO2C
HO OO
AcHN
HOHO
40
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31
9.5 9.0 8.5 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
(600 MHz, D2O)
OHO
HO
HO2CO O
OAcHN
OCH3
HOHOO
OAcHN
HOHO
41
OHO
HO
HO2COO
HOAcHN
HOHO
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32
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 -20
(150 MHz, D2O)
OHO
HO
HO2CO O
OAcHN
OCH3
HOHOO
OAcHN
HOHO
41
OHO
HO
HO2COO
HOAcHN
HOHO
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33
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
( 600 MHz, D2O)
OHO
HO
HO2CO
OCH3O
HOHO
HO2CO O
OAcHN
HOHO
42
OHO
HO
HO2CHO O
OAcHN
HOHO
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200 150 100 50 0
( 150 MHz, D2O)
OHO
HO
HO2CO
OCH3O
HOHO
HO2CO O
OAcHN
HOHO
42
OHO
HO
HO2CHO O
OAcHN
HOHO