Starting with D-mannitol, the yield of the synthesis of 3-0-benzyl-sn-glycerol (1) could be improved. The regioselective alkylation of 1 at the primary hydroxy group to the 1-0-alkyl-3-0-benzyl-sn-glycerols 3 was achieved by using the dibutylstannylene protecting group. The 1-0-alkyl-2-0-methyl-snglycerols 4, readily obtainable from 3, were successfully glycosylated under the conditions of the Koenigs-Knorr reaction to give l-O-alkyl-2-O-methyl-3-O-~-~-glycosyl-sn-glycerols.
Due to the versatility of 2-0-benzyl-1-0-hexadecyl-sn-glycerol (7) as building block for various alkyl ether lipids and alkyl ether lyso-lipids, 7 was prepared from D-mannit following two different strategies. The final product 7 was obtained either via the intermediate 1,2-O-isopropylidene-sn-glycerol (1) or via 3,4-O-isopropylidene-~-mannit (8) in an overall yield of 6% or 11%, respectively.
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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