NEW AND FACILE SYNTHETIC ROUTES TO 5-THIOALDOHEXOPYRANOSIDES VIA ALDOSE MONOTHIOACETAL DERIVATIVES

被引:17
作者
HASHIMOTO, H
KAWANISHI, M
YUASA, H
机构
[1] Department of Life Science Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Midori-ku, Yokohama, 227, Nagatsuta
关键词
5-THIOALDOPYRANOSIDE; ACYCLIC MONOTHIOACETAL; DIMETHYLBORON BROMIDE;
D O I
10.1016/0040-4039(91)85047-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new synthetic routes of 5-thioaldohexopyranosides were developed via aldose S-acetyl O-methyl monothioacetals obtained by one-pot treatment of methyl hexopyranosides with dimethylboron bromide and then thiolacetic acid.
引用
收藏
页码:7087 / 7090
页数:4
相关论文
共 16 条
[1]  
ANISUZZAMAN AKM, 1977, CARBOHYD RES, V55, P205
[2]   5-THIO-D-MANNOSE FROM THE MARINE SPONGE CLATHRIA-PYRAMIDA (LENDENFELD) - THE 1ST EXAMPLE OF A NATURALLY-OCCURRING 5-THIOSUGAR [J].
CAPON, RJ ;
MACLEOD, JK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (15) :1200-1201
[3]  
FEATHER MS, 1962, TETRAHEDRON LETT, P667
[4]  
FURHMANN U, 1985, BIOCHIM BIOPHYS ACTA, V825, P95
[5]   STEREOELECTRONIC EFFECTS IN THE RING CLEAVAGE OF METHYL GLYCOPYRANOSIDES USING DIMETHYLBORON BROMIDE [J].
GUINDON, Y ;
ANDERSON, PC .
TETRAHEDRON LETTERS, 1987, 28 (22) :2485-2488
[6]  
HASEGAWA A, 1978, CARBOHYD RES, V63, P131, DOI 10.1016/S0008-6215(00)80937-4
[7]   SYNTHESIS OF 5-THIO-L-FUCOSE AND ITS INHIBITORY EFFECT ON FUCOSIDASE [J].
HASHIMOTO, H ;
FUJIMORI, T ;
YUASA, H .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (05) :683-694
[8]   THE USE OF INHIBITORS IN THE STUDY OF GLYCOSIDASES [J].
LALEGERIE, P ;
LEGLER, G ;
YON, JM .
BIOCHIMIE, 1982, 64 (11-1) :977-1000
[9]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[10]   IMPROVED SYNTHESES OF 5-THIO-D-GLUCOSE [J].
NAYAK, UG ;
WHISTLER, RL .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) :97-&