Synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-glucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside disodium salts, related to heparin biosynthesis

被引：3

作者：

Cipolla, L

Nicotra, F

Lay, L

Lindahl, U

Panza, L

Russo, G

机构：

[1] UNIV MILAN,CNR,CTR STUDIO SOSTANZE ORGAN NAT,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

[2] UNIV UPPSALA,CTR BIOMED,DEPT MED & PHYSIOL CHEM,S-75123 UPPSALA,SWEDEN

来源：

GLYCOCONJUGATE JOURNAL | 1996年 / 13卷 / 06期

关键词：

heparin biosynthesis; carbohydrates; sulfated disaccharides; synthesis;

D O I：

10.1007/BF01053195

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-glucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside 3 and 4 as disodium salts is described. Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside 6 was converted to trichloroacetimidate 20. Glycosylation of 20 with 5 promoted by BF3 . OEt(2) gave disaccharide 21. Deacetylation of 21 followed by monoacetylation of the resultant diol 22 afforded the two monoacetylated disaccharides 23 and 24. Sulfation and deprotection of each disaccharide gave the desired sulfated compounds 3 and 4.

引用

页码：995 / 1003

页数：9

共 50 条

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