AN ELECTROPHILE-MEDIATED CYCLIZATION ON THE 1,6-ANHYDRO-D-GLUCOPYRANOSE FRAMEWORK

被引：21

作者：

LETEUX, C

VEYRIERES, A

ROBERT, F

机构：

[1] UNIV PARIS 06,CHIM GLUCIDES LAB,F-75230 PARIS 05,FRANCE

[2] UNIV PARIS 06,CHIM MET TRANSIT LAB,UA 419,F-75230 PARIS 05,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1993年 / 242卷

关键词：

D O I：

10.1016/0008-6215(93)80026-B

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：

Iodocyclization of O-tributylstannyl-D-glucal with iodine in acetonitrile gave 1,6-anhydro-2-deoxy-2-iodo-beta-D-glucopyranose (1) in high yield. The 3,4-di-O-acetyl derivative of 1 could be converted into the corresponding 2-deoxy compound and into the 2-C-allyl-2-deoxy branched sugar (5) by treatment with tributylstannane and allyltributylstannane, respectively. Controlled alkaline hydrolysis of 5 gave the 4-monoacetyl derivative. Complete hydrolysis of 5 gave the 3,4-diol, which underwent a 5-exo cyclization by treatment with N-bromosuccinimide. H-1 NMR spectroscopy and X-ray analysis showed that the cyclized product has the B3,O conformation in its pyranose ring, which is trans-fused to the newly formed tetrahydrofuran ring.

引用

收藏

页码：119 / 130

页数：12

相关论文

共 35 条

[11] RADICAL REACTIONS IN NATURAL PRODUCT SYNTHESIS [J].

JASPERSE, CP ;

CURRAN, DP ;

FEVIG, TL .

CHEMICAL REVIEWS, 1991, 91 (06) :1237-1286

[12] ASYMMETRIC HALOLACTONIZATION REACTION .2. ELUCIDATION OF GENERAL APPLICABILITY AND MECHANISM OF THE ASYMMETRIC BROMOLACTONIZATION REACTION [J].

JEW, S ;

TERASHIMA, S ;

KOGA, K .

TETRAHEDRON, 1979, 35 (20) :2345-2352

[13] ASYMMETRIC HALOLACTONIZATION REACTION .1. ASYMMETRIC SYNTHESIS OF OPTICALLY-ACTIVE ALPHA,ALPHA-DISUBSTITUTED-ALPHA-HYDROXY ACIDS FROM ALPHA,BETA-UNSATURATED ACIDS BY THE NOVEL USE OF HALOLACTONIZATION REACTION [J].

JEW, S ;

TERASHIMA, S ;

KOGA, K .

TETRAHEDRON, 1979, 35 (20) :2337-2343

[14] ONE ELECTRON C-C BOND FORMING REACTIONS VIA ALLYLSTANNANES - SCOPE AND LIMITATIONS [J].

KECK, GE ;

ENHOLM, EJ ;

YATES, JB ;

WILEY, MR .

TETRAHEDRON, 1985, 41 (19) :4079-4094

[15]

KEGLEVIC D, 1991, 6TH EUR CARB S ED

[16] UTILIZATION OF 1,6-ANHYDROHEXOSES FOR THE PREPARATION OF SOME ALIPHATIC ADENOSINE-ANALOGS [J].

KRECMEROVA, M ;

CERNY, M ;

BUDESINSKY, M ;

HOLY, A .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1989, 54 (10) :2753-2766

[17] PARTIAL HYDROLYSIS OF ACYL 1,6-ANHYDRO-BETA-D-GLUCOPYRANOSE [J].

KUCAR, S ;

ZAMOCKY, J ;

ZEMEK, J ;

ANDERLE, D ;

MATULOVA, M .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1984, 49 (08) :1780-1787

[18]

KUCAR S, 1988, CHEM PAP, V42, P389

[19] SYNTHESIS AND EVALUATION IN ASYMMETRIC HYDROGENATION OF CARBOHYDRATE-DERIVED 1,3-BISPHOSPHINES [J].

LI, CB ;

BERNET, B ;

VASELLA, A ;

BROGER, EA ;

MEILI, A .

CARBOHYDRATE RESEARCH, 1991, 216 :149-169

[20] SOME ASPECTS OF THE ALKYLATION OF EPOXIDES OF 1,6-ANHYDROPYRANOSES [J].

MAGDZINSKI, L ;

FRASERREID, B .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (11) :2819-2825

← 1 2 3 4 →