SYNTHESIS OF METHYL 2,3-DI-O-METHYL-α-d-SIBIROSAMINIDE
Open Access
- 5 July 1980
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 9 (7) , 777-778
- https://doi.org/10.1246/cl.1980.777
Abstract
Methyl 2,3-di-o-methyl-α-d-sibirosaminide (12; methyl 4,6-dideoxy-3-c-methyl-2,3-di-o-methyl-4-methylamino-α-d-altropyranoside) has been synthesized from methyl 4,6-o-benzylidene-3-c-methyl-2-o-methyl-α-d-altropyranoside (2). The introduction of methylamino group at c-4 position was achieved by hydrogenation of methyl 6-deoxy-3-c-methyl-2,3-di-o-methyl-α-d-arabino-hexopyranosid-4-ulose oxime (8) in the ratio of 2.6:1 (altro:ido) followed by N-formylation and reduction.This publication has 3 references indexed in Scilit:
- Schlüsselreaktionen einer synthese des sibirosaminsTetrahedron Letters, 1980
- Branched-chain Sugars. XII. The Stereoselectivities in the Reaction of Methyl 4,6-O-Benzylidene-α- and -β-d-hexopyranosid-3-uloses with DiazomethaneBulletin of the Chemical Society of Japan, 1978
- Osmium-catalyzed vicinal oxyamination of olefins by Chloramine-TThe Journal of Organic Chemistry, 1976