SYNTHESIS OF C-GLYCOSIDES OF N-ACETYLGLUCOSAMINE BY DIRECT ALKYLATION OF 2-AMINO-2-DEOXY-2,3,4,6-TETRA-O-ACETYL GLUCOPYRANOSYL CHLORIDE

被引：26

作者：

KIM, KI ^{[1
]}

HOLLINGSWORTH, RI ^{[1
]}

机构：

[1] MICHIGAN STATE UNIV,DEPT CHEM & BIOCHEM,E LANSING,MI 48824

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)79957-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The beta-isomer of C-glycoside, ethyl 2-acetamino-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosylacetate(3) was prepared stereoselectively in two steps by reaction of 2-acetamino-2-deoxy-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride(4) with potassium diethylmalonate and 18-crown-6, followed by decarboxylation.

引用

页码：1031 / 1032

页数：2

共 4 条

[1] DIASTEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED C-ALPHA-GLYCOSYL DERIVATIVES AND C-BETA-GLYCOSYL DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-D-GLUCOSE
GIANNIS, A
SANDHOFF, K
[J]. CARBOHYDRATE RESEARCH, 1987, 171 : 201 - 210
[2] TOTAL SYNTHESIS OF ESCHERICHIA-COLI LIPID-A, THE ENDOTOXICALLY ACTIVE PRINCIPLE OF CELL-SURFACE LIPOPOLYSACCHARIDE
IMOTO, M
YOSHIMURA, H
SHIMAMOTO, T
SAKAGUCHI, N
KUSUMOTO, S
SHIBA, T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) : 2205 - 2214
[3] CHEMICAL SYNTHESIS OF A BIOSYNTHETIC PRECURSOR OF LIPID-A WITH A PHOSPHORYLATED TETRAACYL DISACCHARIDE STRUCTURE
IMOTO, M
YOSHIMURA, H
YAMAMOTO, M
SHIMAMOTO, T
KUSUMOTO, S
SHIBA, T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) : 2197 - 2204
[4] A CONVENIENT SYNTHESIS OF BOTH THE ANOMERS OF ETHYL (2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSYL)ACETATE
MONTI, D
GRAMATICA, P
SPERANZA, G
MANITTO, P
[J]. TETRAHEDRON LETTERS, 1987, 28 (42) : 5047 - 5048

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