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Synthesis of Vinyl Sulfoxide‐Modified Pent‐2‐enofuranosides and Hex‐2‐enopyranosides and Preliminary Studies of Their Reactivity
Author(s) -
Atta Ananta Kumar,
Dey Debanjana,
Bhaumik Atanu,
Manna Chinmoy,
Pal Tarun K.,
Pathak Tanmaya
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200637
Subject(s) - chemistry , sulfoxide , pyranose , nitromethane , furanose , adduct , diastereomer , reactivity (psychology) , medicinal chemistry , dimethyl sulfoxide , organic chemistry , aldose , stereochemistry , ring (chemistry) , glycoside , medicine , alternative medicine , pathology
Vinyl sulfoxide‐modified pent‐2‐enofuranosides and hex‐2‐enopyranosides have been synthesized by using a controlled oxidation of C‐3‐deoxy‐C‐3‐thioaryl furanosides and pyranosides, respectively, followed by mesylation of the C‐2‐hydroxyl group and elimination. In the furanose system, both diastereomers were formed in almost equal ratio, whereas the pyranose ring imposed diastereoselectivity of oxidation of the sulfur atom to produce only S s isomers in good overall yields. Vinyl sulfoxide‐modified 2‐enofuranosides were treated with NaCH 2 NO 2 to obtain C‐2 branched chain sugars. Furanosyl sulfoxides yielded products that were similar to the adducts obtained by treatment of the corresponding sulfones with nitromethane. The sulfinyl group in thepyranosides influenced the diastereoselectivity of addition to produce adducts that differed from the products obtained from the corresponding vinyl sulfones under similar reaction conditions.