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The synthesis and the 1h- and 13c-nuclear magnetic resonance spectroscopy of the cyclic sulfites of some sugars

✍ Scribed by Yueh Wang; Harry P.C. Hogencamp

Publisher
Elsevier Science
Year
1979
Tongue
English
Weight
490 KB
Volume
76
Category
Article
ISSN
0008-6215

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✦ Synopsis

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Treatment of methyl j?-D-ribofuranoside with thionyl chloride in hexamethylphosphoric triamide gives two diastereoisomeric methyl 5-chloro-5-deoxy-/3-D-ribofuranoside 2,3-cyclic sulfites. Similar cyclic sulfites are formed from benzyl B-Dribofuranoside and 1,4-anhydro-IX.-ribitol. If acetonitrile is substituted for hexamethylphosphoric triamide, the cyclic sullites are the main products, and only traces of the chlorinated sugars are formed. 'H-and 13C-n.m.r.-spectral analysis of these reactions demonstrated that one of the diastereomers preponderates. The structure of these cyclic sul&es was established by comparison of the 'H-n.m.r. spectra with those of the propylene sulfites. Treatment of 1,2-O-isopropylidene-a-D-glucofuranose ( 14) with thionyl chloride in hexamethylphosphoric triamide yields 3-chloro-3deoxy-i,2-U-isopropylidene-a-rX&llofuranose 5,6-cyclic sullite. In contrast to the 2,3-cyclic sulfites, which are stable, the cyclic sulfites derived from 14 slowly decompose at room temperature.

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