Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 1. Stereochemistry of the reactions of d-glucal derivatives with phenylsulfenyl chloride and phenylselenenyl chloride

Autor:	William R. Roush, David P. Sebesta, Chad E. Bennett
Rok vydání:	1997
Předmět:	chemistry.chemical_classification Glycal Stereochemistry Chemistry Organic Chemistry Heteroatom Substituent Glycoside Biochemistry Chloride chemistry.chemical_compound Drug Discovery medicine Stereoselectivity Selectivity Glucal medicine.drug
Zdroj:	Tetrahedron. 53:8825-8836
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(97)90394-x
Popis:	The stereoselectivity of the reactions of d -glucal derivatives with PhSCl and PhSeCl is dependent on the presence of an electronegative heteroatom substituent at C(6) and the nature of the functionality at C(4). The C(6)-substituent influences the conformational preferences of the d -glucal derivatives, and greatest stereoselectivity is obtained with those glycals that preferentially exist in the inverted 5 H 4 half-chair conformation 28b . A polar substituent at C(4) increases the selectivity by stabilizing the episulfonium/episelenonium ion intermediates 31b and 33 .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a27dac147a23288c4c8a303bcb121447 https://doi.org/10.1016/s0040-4020(97)90394-x Zobrazit plný text záznamu Full Text from ScienceDirect