THE PREPARATION OF SOME MERCAPTO MONOSACCHARIDES
- 1 September 1961
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 39 (9) , 1765-1768
- https://doi.org/10.1139/v61-231
Abstract
Methyl 4,6-O-benzylidene-2-benzylthio-2-deoxy-α-D-altropyranoside and methyl 4,6-O-benzyldene-3-benzylthio-3-deoxy-α-D-altropyranoside have been prepared by the reaction of sodium benzylmercaptide with methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside and methyl 2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranoside respectively.These two thio ethers were successfully reduced by sodium in liquid ammonia to methyl 2-deoxy-2-mercapto-α-D-altropyranoside and methyl 3-deoxy-3-mercapto-α-D-altropyranoside. An attempted replacement of the tosyl group in 1,2;5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranose by benzyl mercaptan was unsuccessful.Keywords
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