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Haloenamines -II. A rapid and efficient synthesis of carbohydrate 1,2-orthoesters

✍ Scribed by Beat Ernst; Alain De Mesmaeker; Beatrice Wagner; Tammo Winkler

Book ID
104228309
Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
193 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Carbohydrate exe 1,2-or&esters are obtained in good to excellent yields by treatingjiuanose andpyranose hemiacetalsfirst with 1.1 eq. I-chloro-2,N,N-trimethyl-propenylamine and then with the appropriate alcohols in the presence of NEg.

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We thank Drs. D. H. Huang and G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. We gratefully thank Nicolas Winssinger for helpful discussions and preparation of the selenium bromide resin.