Stereoselective synthesis of alpha-C-(alkynyl)-glycosides via ring-opening of alpha-1,2-anhydrosugars

被引:41
作者
Leeuwenburgh, MA
Timmers, CM
vanderMarel, GA
vanBoom, JH
Mallet, JM
Sinay, PG
机构
[1] LEIDEN UNIV,LEIDEN INST CHEM,NL-2300 RA LEIDEN,NETHERLANDS
[2] ECOLE NORMALE SUPER,DEPT CHIM,F-75231 PARIS 05,FRANCE
关键词
D O I
10.1016/S0040-4039(97)01381-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ring-opening of an alpha-1,2-epoxide function in sugars with lithium alkynyl derivatives in the presence of zinc chloride proceeds with retention of configuration to afford alpha-C-(alkynyl)-glycosides in reasonable yields. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:6251 / 6254
页数:4
相关论文
共 13 条
[1]   AN UNEXPECTED SIALYLATION - TOTAL SYNTHESES OF G(M4) AND A POSITIONAL ISOMER [J].
GERVAY, J ;
PETERSON, JM ;
ORIYAMA, T ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5465-5468
[2]   DIASTEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED C-ALPHA-GLYCOSYL DERIVATIVES AND C-BETA-GLYCOSYL DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-D-GLUCOSE [J].
GIANNIS, A ;
SANDHOFF, K .
CARBOHYDRATE RESEARCH, 1987, 171 :201-210
[3]   PREFERRED CONFORMATION OF C-GLYCOSIDES .7. PREFERRED CONFORMATION OF CARBON ANALOGS OF ISOMALTOSE AND GENTIOBIOSE [J].
GOEKJIAN, PG ;
WU, TC ;
KANG, HY ;
KISHI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6422-6434
[4]  
IHARA M, 1993, ANGEW CHEM INT EDIT, V32, P1010, DOI 10.1002/anie.199310101
[5]  
MARTIN OR, 1993, SYNLETT, P165
[6]   SAMARIUM IODIDE INDUCED INTRAMOLECULAR C-GLYCOSIDE FORMATION - EFFICIENT RADICAL FORMATION IN THE ABSENCE OF AN ADDITIVE [J].
MAZEAS, D ;
SKRYDSTRUP, T ;
DOUMEIX, O ;
BEAU, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (13) :1383-1386
[7]   THE 1ST SYNTHESIS OF A C-DISACCHARIDE [J].
ROUZAUD, D ;
SINAY, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (22) :1353-1354
[8]  
SUN KM, 1987, CARBOHYD RES, V171, P36
[9]   ENANTIOMERIC SYNTHESIS OF PYRAN SUBUNITS OF MARINE TRANS-FUSED POLYETHER TOXINS - EPIMERIZATION OF ALKYNYL SUGARS THROUGH COBALT COMPLEXES [J].
TANAKA, S ;
ISOBE, M .
TETRAHEDRON, 1994, 50 (19) :5633-5644
[10]  
TIMMERS CM, 1993, RECL TRAV CHIM PAY B, V112, P609