Periodate → (-)-2,3-O-Isopropylidene-D-threitol

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Reaction Steps

Such a reaction sequence is illustrated for R=methyl by way of example in Scheme 1, for the preparation of the (4R, 5R)-compound. The starting material, the known 3,4-O-isopropylidene-D-mannitol (1), is reacted with periodate ion, and the product of glycol cleavage is reduced with sodium borohydride to afford 2,3-O-isopropylidene-D-threitol (2). Sulphonylation of (2) with methanesulphonyl chloride affords the di-methanesulphonate (3), which undergoes displacement with azide ion to yield the diazide(4). Catalytic reduction of (4) gives the (4R,5R)-diamine (5), which is reacted, generally without isolation, with potassium tetrachloroplatinate, to afford (4R,5R)-(I).

Provenance & Evidence