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ChemInform Abstract: Highly Diastereoselective Synthesis of Anomeric β-O- Glycopyranosyl Carbamates from Isocyanates.

✍ Scribed by R. G. G. LEENDERS; R. RUYTENBEEK; E. W. P. DAMEN; H. W. SCHEEREN

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

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✦ Synopsis

Highly Diastereoselective Synthesis of Anomeric β-O-Glycopyranosyl Carbamates from Isocyanates.

-Isocyanates (II) react with anomerically unprotected glycopyranosides ( cf. (I)) to yield the corresponding urethanes with high β-selectivity. The method can also be applied to isocyanates, generated in situ from the carboxylic acids (IV) and diphenylphosphoryl azide at elevated temperature. -(LEENDERS, R.

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A Highly Diastereoselective Synthesis of α-Substituted-β-hydroxy Compounds from Corresponding β-Stannyl Compounds. -Anti compounds, e.g. (II), are completely converted to their syn analogues (IV) using Lewis acids such as SnCl 4 or TiCl 4 . AlCl 3 , ZrCl 4 , or ZnCl 2 are not suitable for this reac