Manipulation of free carbohydrates via stannylene acetals. Preparation of beta-per-O-acyl derivatives of D-mannose, L-rhamnose, 6-O-trityl-D-talose, and D-lyxose

被引:16
作者
Hodosi, G [1 ]
Kovac, P [1 ]
机构
[1] NIDDK,NIH,BETHESDA,MD 20892
关键词
stannylene complexes; 1,2-O-cis-stannylene acetals; beta-mannose; beta-rhamnose; beta-talose; beta-lyxose;
D O I
10.1016/S0008-6215(97)00155-9
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
A simple and high-yielding method for the preparation of 1-O-beta-acyl derivatives of carbohydrates with an axial OH group at C-2 is described. It utilizes the property of unprotected carbohydrates to preferentially form 1,2-O-cis stannylene acetals, when treated with dibutyltin oxide. These acetals can be acylated with retention of configuration at the anomeric position. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:239 / 243
页数:5
相关论文
共 21 条
[1]  
ANGYL SJ, 1972, CARBOHYDRATES A, V1, P195
[2]  
Collins P.M., 1995, MONOSACCHARIDES THEI, P360
[3]  
Fischer E, 1913, BER, V46, P4029
[4]  
GRINDLEY TB, 1994, ACS SYM SER, V560, P51
[5]   TEUCRIOSIDE, A PHENYLPROPANOID GLYCOSIDE FROM TEUCRIUM-CHAMAEDRYS [J].
GROSS, GA ;
LAHLOUB, MF ;
ANKLIN, C ;
SCHULTEN, HR ;
STICHER, O .
PHYTOCHEMISTRY, 1988, 27 (05) :1459-1463
[6]   A fundamentally new, simple, stereospecific synthesis of oligosaccharides containing the beta-mannopyranosyl and beta-rhamnopyranosyl linkage [J].
Hodosi, G ;
Kovac, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2335-2336
[7]  
HODOSI G, IN PRESS J CARBOHYDR
[8]  
Hudson C. S., 1915, J. Am. Chem. Soc, V37, P1264, DOI DOI 10.1021/JA02170A025
[9]   Two forms of anhydrous l-rhamnose and a new method for the preparation of crystalline 0-tetraacetyl-l-rhamnose [J].
Jackson, EL ;
Hudson, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :1076-1078
[10]   SYNTHESIS OF LIGANDS RELATED TO THE O-SPECIFIC ANTIGEN OF TYPE-1 SHIGELLA-DYSENTERIAE .3. GLYCOSYLATION OF 4,6-O-SUBSTITUTED DERIVATIVES OF METHYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE WITH GLYCOSYL DONORS DERIVED FROM MONOSACCHARIDES AND OLIGOSACCHARIDES [J].
KOVAC, P ;
EDGAR, KJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2455-2467