Accession Number:

AD0429749

Title:

NUCLEOPHILIC REACTIONS IN CARBOHYDRATE CHEMISTRY.

Descriptive Note:

Final technical rept., 1 Nov 62-31 Oct 63,

Corporate Author:

LEICESTER UNIV (ENGLAND)

Personal Author(s):

Report Date:

1963-10-31

Pagination or Media Count:

30.0

Abstract:

The powerfully nucleophilic azide ion was used in the preparation of epimino-, diamino-, and aminomercapto-sugar derivatives. Methyl 4,6-0-benzylidene-2, 3-dideoxy 2, 3-epimino-alpha-D-alloside, and the corresponding mannoside were prepared in excellent yield from the corresponding manno- and allo-epoxides. Methyl 3-azido-3-deoxy-alpha-Daltroside 2-toluene-p-sulfonate and the corresponding 2-azido altroside 3-toluene-p-sulfonate were prepared by acid hydrolysis of 4,6-0-benzylidene compounds. Treatment of these compounds with methanolic hydrazine-hydrate-Raney nickel bave the two 4,6-hydroxy epimines. Treatment of methyl 2, 3-anhydro-4, 6-0-benzylidene-alpha-Dmannoside with thiourea in boiling ethanol gave the 2, 3-epithio-alloside in one step. Author

Subject Categories:

Distribution Statement:

APPROVED FOR PUBLIC RELEASE