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ChemInform Abstract: Synthesis of Amino Sugars Through a Highly Diastereoselective Dipolar Cycloaddition. Enantioselective Synthesis of the Carbohydrate Segment of Sch 38516.

✍ Scribed by Z. XU; C. W. JOHANNES; D. S. LA; G. E. HOFILENA; A. H. HOVEYDA

Book ID: 101858617
Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199811231

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✦ Synopsis

Synthesis of Amino Sugars Through a Highly Diastereoselective Dipolar Cycloaddition. Enantioselective Synthesis of the Carbohydrate Segment of Sch 38516.

-The key steps in the synthesis of the amino sugar (VII), a unit of Sch 38516, are diastereoselective cycloaddition of the carbonate (V) to the nitrone (IV) and ring closure of the deprotected analogue of the adduct (VI). Additionally, it is shown that the cycloaddition of nitrones containing a (S)-α-methylbenzyl or a benzyl group proceeds with significant lower diastereoselectivity.

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