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POTENTIAL ANTIRADIATION DRUGS. III. /cap beta/-AMINOMERCAPTANS DERIVED FROM D-ALTROSE

Journal Article · · Journal of the American Chemical Society (U.S.)
DOI:https://doi.org/10.1021/ja01479a023· OSTI ID:4825477
Two methods were explored for the preparation of a glycoside of 3-amino- 2,3-dideoxy-2-mercapto-D-altrose. In the first, unsuccessful approach, a synthesis for the unique sugar episulfide VI was developed. Ammonolysis of VI, however, afforded polymeric products containing amino and mercaptan groups. The successful approach employed a trans-benzylthiotosylate(XVII) which was converted to a trans-benzylthioazide(XIX). A change of blocking groups gave the trans- benzylthioazide XXIII, which, treated with sodium and liquid ammonia and the product XXII deblocked with methanolic hydrogen chloride, afforded the desired aminomercapto glycoside (XXI, R = CH/sub 3/). (auth)
Research Organization:
Stanford Research Inst., Menlo Park, Calif.
Sponsoring Organization:
USDOE
NSA Number:
NSA-15-032060
OSTI ID:
4825477
Journal Information:
Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Vol. Vol: 83; ISSN JACSA
Country of Publication:
Country unknown/Code not available
Language:
English