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Zur stereoselektiven Synthese von 1-O-Alkyl-3-O-benzyl-sn-glycerolen und 1-O-Alkyl-2-O-methyl-3-O-β-D-glycosyl-sn-glycerolen

✍ Scribed by Bauer, Friederike ;Rueß, Klaus-Peter ;Liefländer, Manfred

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
396 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Stereoselective Synthesis of 1‐O‐Alkyl‐3‐O‐benzyl‐sn‐glycerols and 1‐O‐Alkyl‐2‐O‐methyl‐3‐O‐β‐D‐glycosyl‐sn‐glycerols

Starting with D‐mannitol, the yield of the synthesis of 3‐O‐benzyl‐sn‐glycerol (1) could be improved. The regioselective alkylation of 1 at the primary hydroxy group to the 1‐O‐alkyl‐3‐O‐benzyl‐sn‐glycerols 3 was achieved by using the dibutylstannylene protecting group. The 1‐O‐alkyl‐2‐O‐methyl‐sn‐glycerols 4, readily obtainable from 3, were successfully glycosylated under the conditions of the Koenigs‐Knorr reaction to give 1‐O‐alkyl‐2‐O‐methyl‐3‐O‐β‐D‐glycosyl‐sn‐glycerols.

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