BRANCHED-CHAIN SUGARS .14. SYNTHESIS OF NEW BRANCHED-CHAIN CYCLITOLS HAVING MYO-CONFIGURATION OR SCYLLO-CONFIGURATION, AND MUCO-CONFIGURATION FROM 3-O-BENZYL-5,6-DIDEOXY-5-C-(1,3-DITHIAN-2-YL)-6-NITRO-L-IDOFURANOSE AND D-GLUCOFURANOSE

被引：14

作者：

FUNABASHI, M

YOSHIMURA, J

机构：

[1] Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology, Nagatsuta, Midori-ku

[2] Chiba University, College of Arts and Sciences, Chiba-shi 280, Yayoi-cho

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 06期

关键词：

D O I：

10.1039/p19790001425

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition of 2-lithio-1,3-dithian to 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-.alpha.-D-xylo-hex-5-enofuranose (1) gives 3-O-benzyl-5,6-dideoxy-5-C-(1,3-dithian-2-yl)-1,2-O-isopropylidene-6-nitro-.beta.-L-idofuranose (2) and -.alpha.-D-glucofuranose (3) in the ratio 4:3, respectively. Removal of the isopropylidene group and intramolecular cyclization in weak basic conditions gives branched-chain cyclitols having myo- or scyllo-configuration from (2) and muco-configuration from (3). The mechanism of cyclization is discussed. Some biologically active branched-chain cyclitols and analogous compounds were successively found, whereas there are few methods available for the synthesis of such optically active branched-chain cyclitols.

引用

页码：1425 / 1429

页数：5

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