(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol → Dibenzyl 2,3,4-tri-O-benzyl-beta-L-fucopyranosyl phosphate

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Reaction Steps

A solution of 2,3,4-tri-O-benzyl-L-fucopyranose (0.50 g, 0.86 mmol) in 20 ml of dry dichloromethane and freshly recrystallized dibenzyl phosphate (0.24 g, 0.86 mmol) is stirred under a nitrogen atmosphere at room temperature for about 1 h. The solution is then concentrated and purified by chromatography (toluene/acetone 7:1). Dibenzyl 2,3,4-tri-O-benzyl-β-L-fucopyranosyl phosphate (5) is obtained in a yield of 95% as a colorless oil (0.57 g). TLC (toluene/acetone 7:1 gives an Rf of 0.45, [α]578 =-9.7 (c=1, chloroform).

Provenance & Evidence