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Syntheses of methyl 2,6-diacetamido-2,3,6-trideoxy-α-d-ribo-hexopyranoside (methyl di-N-acetyl-α-d-tobrosaminide) and methyl 2-acetamido-2,3,6-trideoxy-β-l-lyxo-hexopyranoside

✍ Scribed by Mohammed M. Abuaan; John S. Brimacombe; Leslie C.N. Tucker

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
612 KB
Volume
132
Category
Article
ISSN
0008-6215

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✦ Synopsis

The title glycosides were synthesised from D-glUCOSe, via the common intermediate methyl 2-acetamido-4-O-benzoyld-bromo-2,3,6-trideoxy-a-D-ribohexopyranoside . *To whom enquiries should be addressed. **The overall efficiency of this procedure can be improved by using a phase-transfer process' in the preparation of methyl 4,6-O-benzylidene-2-O-toluene-p-sulphonyl-~-n-glu~pyranoside.

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ABSTRACf Previously unknown methyl 2,3-diacetamido-2,3-dideoxy-a-D-hexopyranosides having the gulo, allo, galacto, ido, and altro configurations, as well as 2,3-diacetamido-2,3-dideoxy-D-galactose, have been synthesised. 13C-N.m.r. data for all eight methyl 2,3-diacetamido-2,3-dideoxy-cu-D-hexopyran