FORMATION OF EPOXIDES FROM SUBSTITUTED HEXITOLS

被引:46
作者
JARMAN, M
ROSS, WCJ
机构
[1] Chester Beatty Research Institute, Institute of Cancer Research: Royal Cancer Hospital, Fulham Road
基金
英国医学研究理事会;
关键词
D O I
10.1016/S0008-6215(00)82130-8
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
1,6-Dibromo-1,6-dideoxygalactitol (2), 1-O-methanesulphonyl-D-mannitol (5), and 3,4-di-O-methanesulphonyl-D-mannitol (8) were respectively converted at nearly neutral pH into 1,2:5,6-dianhydrogalactitol (4), 1,2-anhydro-D-mannitol (6), and 2,3:4,5-dianhydro-D-iditol (9). Strongly alkaline conditions yielded 2,3:4,5-dianhydro-L-iditol (7) from 1,6-di-O-methanesulphonyl-D-mannitol (1). The structures of compounds 4, 6, 7, and 9 were confirmed by p.m.r. spectroscopy, and by their reactivity towards thiosulphate and iodide ions. The conversion of 1,2:5,6-dianhydro-D-mannitol (3) into 1,6-dideoxy-1,6-diiodo-D-mannitol, 1,6-dibromo-1,6-dideoxy-D-mannitol, and 1,6-di-O-benzoyl-D-mannitol, and 1,2:5,6-dianhydrogalactitol into 1,6-dideoxy-1,6-diiodogalactitol is described. © 1969.
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页码:139 / &
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