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2005
Carbohydrates
U 0500
Protic Acid (HClO4 Supported on Silica Gel)-Mediated Synthesis of 2,3-Unsaturand a Chiral Furan Diol from 2,3-Glycals. — HClO4 supported
01- 176 ated-O-glucosides
on silica gel is found to be an efficient reagent for fast and stereoselective conversion
of glycals into 2,3-unsaturated-O-glucosides which are useful synthetic synthons. Different alcohols as well as thiols smoothly react under these conditions. Interestingly,
coupling with β-naphthol gives the C-glucoside (VII) instead of the corresponding
O-glucoside. Starting from unprotected D-glucal as well as D-galactal, the chiral furan
diol (IX) is obtained. — (AGARWAL, A.; RANI, S.; VANKAR*, Y. D.; J. Org.
Chem. 69 (2004) 18, 6137-6140; Dep. Chem., Indian Inst. Technol., Kanpur 208 016,
India; Eng.) — Jannicke
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