Accession Number:

AD0404186

Title:

NUCLEOPHILIC REACTIONS IN CARBOHYDRATE CHEMISTRY

Descriptive Note:

Final technical rept., 1 Nov 1961-31 Oct 1962

Corporate Author:

LEICESTER UNIV (UNITED KINGDOM)

Personal Author(s):

Report Date:

1962-10-31

Pagination or Media Count:

27.0

Abstract:

Nucleophilic N3, SCN, and RS ions reactions were made with carbohydrate molecules. Methyl 2,3-anhydro-4,6-O-benzylidene-alpha-D-mannoside with sodium azide in boiling 2-methoxyethanol gave methyl 3-azido-4,6-O- benzylidene-3-deoxy alpha-D-altroside. Reaction on the corresponding anhydro- alloside gave predominantly methyl 2 azido-4,6-O-benzylidene-2-deoxy-alpha-D- altroside I with a lesser amount of the 3-azido-3-deoxy D-glucose isomer. All three azido sugars were characterized by reduction to the corresponding, known, amino sugars. The azido-altrosides were reduced to the corresponding amino, o sulphonate derivatives. ous attempts were made to convert these compounds into 2,3-imino compounds. N2H4 in the presence of Raney Ni yielded methyl 4,6-O- benzylidene-2,3-dideoxy-2,3-imino-alpha-D- mannoside which was converted into the corresponding 2,3-acetimido, and 2,3-benzimido derivatives. Methyl 2,3- diazido-4,5-O-benzylidene-2,3-di deoxy-alpha-D-mannoside was prepared by direct S sub N2 replacement on the 3-sulphonate of I

Subject Categories:

  • Biochemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE