Elsevier

Carbohydrate Research

Volume 222, 30 December 1991, Pages 57-68
Carbohydrate Research

Synthesis of 2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-3-O-[(3R)-3-hydroxytetradecanyl]-α-d-glucopyranosyl dihydrogen phosphate and 2-deoxy-2-[(3R)-3-hydroxy-tetradecanamido]-3-O-[3R)-3-hydroxytetradecanyl]-4-O-phosphono-d-glucopyranose

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Abstract

Both a 3-O-alkyl lipid X analogue and its 4-O-phosphono isomer were synthesized from allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-α-d-glucopyranoside.

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    The anomeric allyl protecting groups of 7a and 7b were deprotected to give 8a and 8b, respectively, by treatment with SeO2 for 8a from 7a, or by treatment with 1,5-cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate13 as a catalyst, and successive treatment with water–pyridine–iodine for 8b from 7b. The reaction of 8a and 8b with trichloroacetonitrile and a catalytic amount of 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) gave an anomeric mixture of trichloroacetimidates 9a and 9b, respectively.14 The anomeric α-cyanation was performed by a previously reported method.15

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