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The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin by Horst Böshagen; Fred-Robert Heiker; A. Matthias Schüller is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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The synthesis of 2-acetamido-1 ,Zdideoxynojirimycin (Zacetamido-1,2,5-trideoxy-1,5-imino-D-glucitol) by a double inversion procedure starting from l-deoxynojirimycin is reported. The key intermediates were the selectively protected N-benzyl-l,5-dideoxy-l,5-imino-4,6-0-isopropylidene-~-mannitol, the triflate ester Nbenzyl -3 -0 -benzyl -1,5 -dideoxy -1.5 -imino -4,6 -0 -isopropylidene -2 -0 -(trifluoromethylsulfonyl)-D-mannitol, and 2-azido-N-benzyl-3 -0-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol, readily obtained in a sequence from l-deoxynojirimycin. Thus I-deoxynojirimycin served as a synthon compatible with the basic operations of carbohydrate chemistry. \*Dedicated to my respected teacher Prof. Burckhardt Helferich on the occasion of his 100th anniversary.

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Author

Horst Böshagen; Fred-Robert Heiker; A. Matthias Schüller

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1987

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)