STEREOSELECTIVE SYNTHESIS OF 1-O-ALKYL-3-O-BENZYL-SN-GLYCEROLS AND 1-O-ALKYL-2-O-METHYL-3-O-BETA-D-GLYCOSYL-SN-GLYCEROLS

BAUER, F and RUESS, KP and LIEFLANDER, M (1991) STEREOSELECTIVE SYNTHESIS OF 1-O-ALKYL-3-O-BENZYL-SN-GLYCEROLS AND 1-O-ALKYL-2-O-METHYL-3-O-BETA-D-GLYCOSYL-SN-GLYCEROLS. LIEBIGS ANNALEN DER CHEMIE (8). pp. 765-768. ISSN 0170-2041,

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Abstract

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-beta-D-glycosyl-sn-glycerols.

Item Type: Article
Uncontrolled Keywords: ETHER GLYCEROGLYCOLIPIDS; LYSOGLYCOLIPIDS, GLYCERYL ETHERS; STEREOSELECTIVE SYNTHESIS; KOENIGS-KNORR REACTION; GLYCERYL ETHERS
Depositing User: Dr. Gernot Deinzer
Last Modified: 19 Oct 2022 08:46
URI: https://pred.uni-regensburg.de/id/eprint/54934

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