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ChemInform Abstract: Stereoselective Synthesis of 2-Deoxy-β-glycosides from Glycal Precursors. Part 2. Stereochemistry of Glycosidation Reactions of 2- Thiophenyl- and 2-Selenophenyl-α-D-gluco-pyranosyl Donors.

✍ Scribed by W. R. ROUSH; D. P. SEBESTA; R. A. JAMES

Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Stereoselective Synthesis of 2-Deoxy-β-glycosides from Glycal Precursors. Part 2. Stereochemistry of Glycosidation Reactions of 2-Thiophenyl-and 2-Selenophenyl-α-D-gluco-pyranosyl Donors. -The β-D-glucopyranosyl acetates (I) and (II) and the trichloroacetimidates (III) are tested as donors in the synthesis of 2-deoxy-β-glycosides. The most efficient and selective donor is ( IIIb), while (Ib) provides the β-glycosides with excellent selectivity but in modest yields. All other donors are not suited because of poor stereocontrol. -(ROUSH,

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