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
Synthesis and 13C-N.m.r. spectra of methyl 2,3-diacetamido-2,3-dideoxy-α-d-hexopyranosides and 2,3-diacetamido-2,3-dideoxy-d-hexoses
✍ Scribed by Yuriy A. Knirel; Evgeniy V. Vinogradov; Nina A. Kocharova; Alexander S. Shashkov; Boris A. Dmitriev; Nikolay K. Kochetkov
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- English
- Weight
- 612 KB
- Volume
- 122
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
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-hexopyranosides and for three 2,3-diacetamido-2,3-dideoxy-D-hexoses having the gluco, manno, and galacto configurations are reported. The regularity of changes in the spectra of 2,3diacetamido sugars, as compared with those of the parent hexoses, and the calculation of '"C-n.m.r.
spectra of their derivatives, using a method of additive corrections, are discussed.
📜 SIMILAR VOLUMES
1-(2-O-Acetyl-3,5,6-tri-O-benzoyl-beta-D-glucofuranosyl)thymine (1) was converted into the 2,2'-anhydro derivative 4 by selective deacetylation, mesylation, and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene. Cleavage of the 2,2'-anhydro ring in 4 with hydrogen bromide or hydrogen chloride led to