SYNTHESIS OF 5-THIOALDOPENTOPYRANOSIDE VIA DITHIOACETAL REARRANGEMENT AND GLYCOSIDATION TO GIVE PSEUDODISACCHARIDES

被引:20
作者
LEPINE, C [1 ]
ROY, C [1 ]
DELORME, D [1 ]
机构
[1] MERCK FROSST CTR THERAPEUT RES,POINTE CLAIRE H9R 4P8,PQ,CANADA
关键词
D O I
10.1016/S0040-4039(00)73176-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rearrangement of acetylated 5-O-p-toluenesulfonyl-L-arabinose dibenzyl dithioacetal 10 gave benzyl 1,5-dithio-L-arabinopyranoside 6 which upon anomeric bromination followed by glycosidation led to pseudodisaccharide 20 containing a sulfur atom in the ring of the non-reducing unit Similarly, benzyl 1,5-dithio-D-lyxopyranoside 17 was obtained from 5-O-p-tolueresulfonyl-D-lyxose dibenzyl dithioacetal 16.
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页码:1843 / 1846
页数:4
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