Synthesis and biological activity of the (-)-(2R,3S,4S)-3-azido-4-methoxy-2-(1′S-methoxy-2′-azido)ethyl-thiolane

被引:10
作者
Arcelli, A
Cerè, V
Peri, F
Pollicino, S
Sabatino, P
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
[2] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
D O I
10.1016/S0957-4166(00)00071-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A stereospecific ring contraction reaction, promoted by NaN3, was detected starting from a thiepane derivative obtained from D-sorbitol, an inexpensive alcohol sugar. The major polyfunctionalized thiolane derivative obtained was investigated as a potential glycosidase inhibitor. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1389 / 1395
页数:7
相关论文
共 22 条
[11]   Synthesis of thiosugars as weak inhibitors of glycosidases [J].
LeMerrer, Y ;
Fuzier, M ;
Dosbaa, I ;
Foglietti, MJ ;
Depezay, JC .
TETRAHEDRON, 1997, 53 (49) :16731-16746
[12]   Synthesis of five-membered homothiosugars derived from L-erythrose and D-mannose [J].
Riedner, J ;
Robina, I ;
Fernández-Bolaños, JG ;
Gómez-Bujedo, S ;
Fuentes, J .
TETRAHEDRON-ASYMMETRY, 1999, 10 (17) :3391-3401
[13]   Synthesis and biological evaluation of the L-enantiomer of 2'-deoxy-5-ethyl-4'-thiouridine [J].
Selwood, DL ;
Carter, K ;
Young, RJ ;
Jandu, KS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (08) :991-994
[14]  
SHELDRICK GM, 1993, SHELXL 93 PROGRAM RE
[15]   (1R,2S,4S,7AR)-1,2-DIHYDROXY-7-THIA-3A-THIONIAPERHYDROPENTALENE CHLORIDE - A NEW, BIOLOGICALLY-ACTIVE PYRROLIZIDINE ALKALOID ANALOG [J].
SIRIWARDENA, AH ;
CHIARONI, A ;
RICHE, C ;
ELDAHER, S ;
WINCHESTER, B ;
GRIERSON, DS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (20) :1531-1533
[16]  
Spek A., 1990, ACTA CRYSTALLOGR, V46
[17]   A SIMPLE HIGHLY EFFICIENT ASYMMETRIC-SYNTHESIS - PREPARATION AND ABSOLUTE-CONFIGURATION OF 3(S)-(TERT-BUTOXYCARBONYLAMINO)-1(S)-METHYLTETRAHYDROTHIOPHENIUM TOSYLATE [J].
TANI, K ;
OTSUKA, S ;
KIDO, M ;
MIURA, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (24) :7394-7396
[18]   SYNTHESIS OF OPTICALLY-ACTIVE 3(R)-[(ALKYLSULFONYL)OXY]THIOLANES FROM 2(R)-HYDROXY-4-(METHYLTHIO)BUTANOIC ACID OR D-METHIONINE [J].
URBAN, FJ ;
BREITENBACH, R ;
VINCENT, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3670-3672
[19]   AMINO-SUGAR GLYCOSIDASE INHIBITORS - VERSATILE TOOLS FOR GLYCOBIOLOGISTS [J].
WINCHESTER, B ;
FLEET, GWJ .
GLYCOBIOLOGY, 1992, 2 (03) :199-210
[20]   Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the ayurvedic traditional medicine Salacia reticulata in Sri Lanka and India [J].
Yoshikawa, M ;
Murakami, T ;
Shimada, H ;
Matsuda, H ;
Yamahara, J ;
Tanabe, G ;
Muraoka, O .
TETRAHEDRON LETTERS, 1997, 38 (48) :8367-8370