期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 2, 页码 773-781出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo8022439
关键词
-
资金
- NIH [GM57335, GM62160]
The synthesis of both enantiomers of a 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycoside is described starting from D-mannnose and L-arabinose derivatives for the D- and L-series, respectively. This donor is effective in the preparation of the corresponding beta-glycosides using the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride protocol. Following desulfurization and concomitant debenzylation with Raney nickel, the so-formed 6-thio-beta-mannosides are converted in high yield to the beta-rhamnopyranosides.
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