Mannitol → Mannitol

HRID 1073452Notes

Reaction equation

HRID 1073452 reaction equation
[CH2:1]([OH:12])[C@H:2]([C@H:4]([C@@H:6]([C@@H:8]([CH2:10][OH:11])[OH:9])[OH:7])[OH:5])[OH:3].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([OH:12])[C@@H:2]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@@H:4]1[OH:5].[CH2:10]([OH:11])[C@H:8]([C@H:6]([C@@H:4]([C@@H:2]([CH2:1][OH:12])[OH:3])[OH:5])[OH:7])[OH:9]

Participants

5

Reactant 2

HCID 6251MannitolHCID 11430Potassium Carbonate

Product 2

HCID 6251MannitolHCID 1764652,5-Sorbitan

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The title compound was prepared by a modification of the method of T. A. W. Koerner, et al., Carbohydrate Research, 59, 403-416 (1977). Acidic dehydration of D-mannitol and isopropylidenation of the mixture of anhydrides gave a dark syrup. A solution of the syrup in acetone was stirred over potassium carbonate, filtered and evaporated. The desired isopropylidene derivative of anhydroglucitol was isolated by HPLC (silica gel, 28% yield from D-mannitol) without going through the trityl derivative. Hydrolysis of the isopropylidene gave 2,5-anhydro-D-glucitol.

Workup

  1. customgave a dark syrup
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-db51a45155994d92ad610c9b9f24aac0
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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