SYNTHESIS OF TERMINAL OLIGOSACCHARIDES FROM TYPE-SPECIFIC LIPOOLIGOSACCHARIDE OF MYCOBACTERIUM-TUBERCULOSIS

被引：5

作者：

GURJAR, MK

DAS, SK

MAINKAR, PS

机构：

[1] Indian Institute of Chemical Technology, Hyderabad

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1994年 / 13卷 / 06期

关键词：

D O I：

10.1080/07328309408011690

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 coupling reaction between 1,3-di-O-acetyl-4-O-benzyl-2-O-methyl-alpha-L-rhamnopyranose (9) and methyl 4-O-benzyl-2-O-methyl-alpha-L-rhamnopyranoside (4) was carried out in the presence of boron trifluoride-etherate followed by deacetylation to give the disaccharide (11) containing a free 3' position. The second glycosylation reaction with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of mercuric salts followed by removal of benzyl and acetyl groups provided the trisaccharide 2. The boron trifluoride catalysed condensation of 1,3,4-tri-O-acetyl-2-O-methyl-L-fucopyranose (14) and methyl 2,4,6-tri-O-benzyl-alpha-D-glucopyranoside (15) gave the disaccharide (16) from which the protecting groups were removed to form the disaccharide (3).

引用

收藏

页码：899 / 907

页数：9

相关论文

共 11 条

[1] SELECTIVE CLEAVAGE OF ALLYL ETHERS UNDER MILD CONDITIONS BY TRANSITION-METAL REAGENTS [J].

COREY, EJ ;

SUGGS, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (18) :3224-3224

[2] NOVEL TYPE-SPECIFIC LIPOOLIGOSACCHARIDES FROM MYCOBACTERIUM-TUBERCULOSIS [J].

DAFFE, M ;

MCNEIL, M ;

BRENNAN, PJ .

BIOCHEMISTRY, 1991, 30 (02) :378-388

[3] SYNTHESIS OF ME ALPHA-L-RHAP-(1-])-2-O-ME-ALPHA-L-RHAP AND ME 2,3,4-TRI-O-ME-ALPHA-L-FUCP-(1-]3)-ALPHA-L-RHAP-(1-]3)-2-O-ME-ALPHA-L-RHAP - OLIGOSACCHARIDE SEGMENTS OF PHENOLIC GLYCOLIPIDS IN MYCOBACTERIUM-BOVIS BCG AND TUBERCULOSIS STRAIN CANETTI [J].

GURJAR, MK ;

VISWANADHAM, G .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1991, 10 (03) :481-485

[4] SYNTHESIS OF METHYL 3-O-(2-O-METHYL-ALPHA-L-FUCOPYRANOSYL)-ALPHA-L-RHAMNOPYRANOSIDE, METHYL 3-O-ALPHA-L-RHAMNOPYRANOSYL-ALPHA-D-GLUCOPYRANOSIDE, AND METHYL 3-O-[3-O-(2-O-METHYL-ALPHA-L-FUCOPYRANOSYL)-ALPHA-L-RHAMNOPYRANOSYL]-ALPHA-L-RHAMNOPYRANOSIDE - DISACCHARIDE AND TRISACCHARIDE SEGMENTS OF A LIPO-OLIGOSACCHARIDE (LOS-1) OF MYCOBACTERIUM-SZULGAI [J].

GURJAR, MK ;

MAINKAR, PS .

CARBOHYDRATE RESEARCH, 1993, 239 :297-304

[5] SYNTHESIS OF METHYL 2,4-DI-O-METHYL-3-O-(2-O-METHYL-ALPHA-L-RHAMNOPYRANOSYL)-ALPHA-L-RHAMNOPYRANOSIDE AND METHYL 2,4-DI-O-METHYL-3-O-[2-O-METHYL-3-O-(2-O-METHYL-ALPHA-L-FUCOPYRANOSYL)-ALPHA-L-RHAMNOPYRANOSYL]-ALPHA-L-RHAMNOPYRANOSIDE - DISACCHARIDE AND TRISACCHARIDE SEGMENTS OF A PHENOLIC GLYCOLIPID OF MYCOBACTERIUM-KANSAII [J].

GURJAR, MK ;

REDDY, KR .

CARBOHYDRATE RESEARCH, 1992, 226 (02) :233-238

[6] TREHALOSE-CONTAINING LIPOOLIGOSACCHARIDES FROM MYCOBACTERIA - STRUCTURES OF THE OLIGOSACCHARIDE SEGMENTS AND RECOGNITION OF A UNIQUE N-ACYLKANOSAMINE-CONTAINING EPITOPE [J].

HUNTER, SW ;

JARDINE, I ;

YANAGIHARA, DL ;

BRENNAN, PJ .

BIOCHEMISTRY, 1985, 24 (11) :2798-2805

[7] SYNTHESIS OF METHYL 2,4,6-TRI-O-BENZYL ALPHA D-GLUCOPYRANOSIDE [J].

KOTO, S ;

TAKEBE, Y ;

ZEN, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (01) :291-+

[8]

MAINKAR PS, 1992, THESIS OSMANIA U

[9] SYNTHESIS OF OLIGOSACCHARIDES CORRESPONDING TO BIOLOGICAL REPEATING UNITS OF SHIGELLA-FLEXNERI VARIANT Y-POLYSACCHARIDE .1. OVERALL STRATEGY, SYNTHESIS OF A KEY TRISACCHARIDE INTERMEDIATE, AND SYNTHESIS OF A PENTASACCHARIDE [J].

PINTO, BM ;

MORISSETTE, DG ;

BUNDLE, DR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :9-14

[10]

Roth W., 1963, METHODS CARBOHYDR CH, V2, P405