ISSN:
0170-2041
Keywords:
Lysoglycolipids, glyceryl ethers
;
Stereoselective synthesis
;
Koenigs-Knorr reaction
;
Glyceryl ethers
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Stereoselective Synthesis of 1-O-Alkyl-3-O-benzyl-sn-glycerols and 1-O-Alkyl-2-O-methyl-3-O-β-D-glycosyl-sn-glycerolsStarting 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101131
