Periodate → 73346-74-4

HRID 2231623Notes

Reaction equation

HRID 2231623 reaction equation
[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]([C@H:7]([OH:10])CO)[C@@H:4]([C@H:11]([OH:14])CO)[O:3]1.I([O-])(=O)(=O)=O.[BH4-].[Na+]>>[CH3:1][C:2]1([CH3:15])[O:3][C@H:4]([CH2:11][OH:14])[C@@H:5]([CH2:7][OH:10])[O:6]1

Participants

4

Reactant 3

HCID 167232PeriodateHCID 4311764Sodium borohydrideHCID 7096260HCID 7096260, compound

Product 1

HCID 78524473346-74-4

Procedure

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).

Sources & evidence

ORD record
ord-c18c5026a8fe49589de0c4af1c03a98d
Source dataset
uspto-grants-1988_11
Patent number
US04783452

Reaction notes

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