ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Glycosylimidates, 8. - Synthesis of 1-ThioglycosidesAs expected. the reactive acetyl-protected O-(α-D-glucopyranosyl) trichloroacetimidate 3 reacts with S-nucleophiles and trifluoroborane-ether as catalyst to yield exclusively 1-thio-β-D-glucopyranosides with inversion of the configuration. The corresponding benzyl-protected α-trichloroacetimidate 4 affords with retention of the configuration alkyl 1-thio-α-D-glucopyranosides. The importance of alkyl 1-thio-β-D-galactopyranosides in enzyme induction was reason to apply this convenient and efficient glycosyl-transfer reaction to the synthesis of isopropyl 1-thio-β-D-galactopyranoside (12a) and the sodium salt of 1-thio-β-D-galactopyranose (12b), respectively.
Notes:
Das reaktive acetylgeschützte O-(α-D-Glucopyransyl)trichloracetimidat 3 liefert mit S-Nucleophilen unter Bortrifluorid-Ether-Katalyse erwartungsgemäß unter Inversion der Konfiguration ausschließlich 1-Thio-β-D-glucopyranoside. Mit dem entsprechenden benzylgeschützten α-Trichloracetimidat 4 werden unter Retention der Konfiguration ausschließlich 1-Thio-α-D-glucopyranoside erhalten. Die Bedeutung von Alkyl-1-thio-β-D-galactopyranosiden zur Enzyminduktion war Anlaß, diese einfache Glycosylübertragung auch zur Synthese von Isopropyl-1-thio-β-D-galactopyranosid (12a) und des Natriumsalzes von 1-Thio-β-D-galactopyranose (12b) anzuwenden.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198319830717
