Production of N-substituted derivatives of 1-desoxynojirimicin

Details Production of N-substituted derivatives of 1-desoxynojirimicin Production of N-substituted derivatives of 1-desoxynojirimicin

1981-09-25

1983-09-20

Shapiro, Lionel M.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing compound containing saccharide radical

546242, C12P 1926, C07D21146

Patent

active

044057148

ABSTRACT:
A process has been developed for the preparation of compounds of the formula ##STR1## wherein R is hydrogen or an optionally substituted alkyl radical, which comprises reacting glucose with a compound of the formula H.sub.2 N-R wherein R has the meaning given above to form a 1-amino-sorbitol of the formula ##STR2## wherein R has the meaning given above,
reacting said 1-aminosorbitol with a compound providing a protective group which can be split off under acid conditions and is stable in the subsequent microbiological oxidation process, aerobically oxidizing the compound thus obtained microbiologically to give a protected 6-aminosorbose, splitting off the protective group under acid conditions and hydrogenating the 6-aminosorbose salt thus obtained either after being isolated or in one operation, to give the compound of the formula (I). The products obtained by the process of the invention are useful as .alpha.-glucoside inhibitors.

REFERENCES:
patent: 4246345 (1981-01-01), Kinast et al.
patent: 4266025 (1981-05-01), Kinast et al.
The Peptides, vol. 1, Gross et al., editors, pp. 42-44 (1979).

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