A convenient synthesis of α- and β-D-glucosamine-1-phosphate and derivatives

被引:20
作者
Busca, P [1 ]
Martin, OR [1 ]
机构
[1] Fac Sci, Inst Chim Organ & Analyt, F-45067 Orleans 2, France
关键词
D O I
10.1016/S0040-4039(98)01838-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Derivatives of alpha- and beta-D-glucosamine-1-phosphate and of alpha-D-galactosamine-1-phosphate, as well as free beta-D-glucosamine-1-phosphate, were prepared stereoselectively and in high yield by way of the opening of the 1,2-oxazoline derived from the corresponding 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-alpha-D-hexopyranosyl bromide with dibenzyl phosphate. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8101 / 8104
页数:4
相关论文
共 21 条
[1]  
BALUJA A, 1960, J CHEM SOC, P4678
[2]   THE USE OF 2-DEOXY-2-TRICHLOROACETAMIDO-D-GLUCOPYRANOSE DERIVATIVES IN SYNTHESES OF OLIGOSACCHARIDES [J].
BLATTER, G ;
BEAU, JM ;
JACQUINET, JC .
CARBOHYDRATE RESEARCH, 1994, 260 (02) :189-202
[3]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF 2-ACETAMIDO-2-DEOXY-D-HEXOSES AND SOME SPECIFICALLY DEUTERIATED, O-ACETYLATED, AND PHOSPHORYLATED DERIVATIVES [J].
BUNDLE, DR ;
JENNINGS, HJ ;
SMITH, ICP .
CANADIAN JOURNAL OF CHEMISTRY, 1973, 51 (22) :3812-3819
[4]   A family of UDP-GalNAc: Polypeptide N-acetylgalactosaminyl-transferases control the initiation of mucin-type O-linked glycosylation [J].
Clausen, H ;
Bennett, EP .
GLYCOBIOLOGY, 1996, 6 (06) :635-646
[5]   NMR STUDY OF EFFECTS OF FLUORINE SUBSTITUENTS ON ASSOCIATION BETWEEN LYSOZYME AND DERIVATIVES OF 2-AMINO-2-DEOXY-D-GLUCOSE [J].
HALL, LD ;
GRANT, CWM .
CARBOHYDRATE RESEARCH, 1972, 24 (01) :218-&
[6]   STRUCTURE AND GLYCOSYLATION OF LIPOTEICHOIC ACIDS IN BACILLUS STRAINS [J].
IWASAKI, H ;
SHIMADA, A ;
YOKOYAMA, K ;
ITO, E .
JOURNAL OF BACTERIOLOGY, 1989, 171 (01) :424-429
[7]  
KHORLIN AY, 1970, TETRAHEDRON LETT, P4803
[8]   MILD, RAPID AND SELECTIVE DEPROTECTION OF ACETYLATED CARBOHYDRATES AND PHENOLS WITH GUANIDINE [J].
KUNESCH, N ;
MIET, C ;
POISSON, J .
TETRAHEDRON LETTERS, 1987, 28 (31) :3569-3572
[9]  
MALTSEV SD, 1988, BIOORG KHIM+, V14, P69
[10]   THE BINDING OF MONOSACCHARIDES TO WHEAT-GERM-AGGLUTININ - FLUORESCENCE AND NMR INVESTIGATIONS [J].
MIDOUX, P ;
GRIVET, JP ;
DELMOTTE, F ;
MONSIGNY, M .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1984, 119 (02) :603-611