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l-Quebrachitol was O-demethylated to give 1l-chiro-inositol which, on treatment with dibutyltin oxide, benzyl chloride, and tetrabutylammonium iodide in acetonitrile, gave mainly crystalline 1l-2,3,5-tri-O-benzyl-chiro-inositol (5a) together with 1l-2,3,5,6-tetra-O-benzyl-chiro-inositol. Catalytic hydrogenolysis of the 1,4,6-tribenzoate (6a) of 5a afforded crystalline (-)-1l-1,4,6-tri-O-benzoyl-chiro-inositol (7). Phosphitylation of 7 with either bis(2-cyanoethyl) N,N-diisopropylphosphoramidite or chlorodiethoxyphosphine followed by oxidation gave the respective 2,3,5-trisphosphate derivatives. Deprotection with either sodium in liquid ammonia or bromotrimethylsilane followed by sodium hydroxide then gave (-)-1l-chiro-inositol 2,3,5-trisphosphate (2). © 1992.

Original publication

DOI

10.1016/0008-6215(92)85042-X

Type

Journal article

Journal

Carbohydrate Research

Publication Date

09/10/1992

Volume

234

Pages

107 - 115