Total Asymmetric-Synthesis of 5-Deoxy-5-Thio-L-Allose

The optically pure Diels-Alder adduct of furan to 1-cyanovinyl (1R)-camphanate was converted to methyl(methyl 5-bromo-5-deoxy-2,3-O-isopropylidene-beta-L-allo-hexo-furanosid)uronate. Ester reduction, followed by HBr elimination afforded (+)-methyl 5,6-anhydro-2,3-O-isopropylidene-D-beta-talo-hexofuranoside. Applying the method of Adley and Owen, (+)-methyl 5,6-dideoxy-5,6-epithio-2,3-O-isopropylidene-L-beta-allo-hexofuranoside was obtained and acetolysed to give, after deprotection, (-)-5-deoxy-5-thio-L-allose.


Published in:
Journal of Carbohydrate Chemistry, 13, 4, 555-563
Year:
1994
ISSN:
0732-8303
Keywords:
Note:
Univ lausanne,chim sect,ch-1005 lausanne,switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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