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A synthesis of methyl 4,6-dideoxy-3-C-methyl-4-(N-methylacetamido)-α-d-altropyranoside, the 3-epimer of (methyl N-acetylsibirosaminide)

✍ Scribed by Michael Georges; Donald MacKay; Bert Fraser-Reid

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
844 KB
Volume
130
Category
Article
ISSN
0008-6215

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✦ Synopsis

The oxirane ring of 1,6:3,4-dianhydro-beta-D-talopyranose reacted at C-4 with methylamine, and the product, further processed gave a 3-deoxy-C-3-methylene derivative. Iodonium ion-induced cyclisation led to an iodooxazolidinone, and deiodination, followed by hydrolysis and N-acetylation, to the title compound.

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