Methanol → Sorbitol

HRID 1270684Notes

Reaction equation

HRID 1270684 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][OH:5]>>[CH2:4]([OH:5])[C@@H:1]([C@H:4]([C@@H:1]([C@@H:4]([CH2:1][OH:2])[OH:5])[OH:2])[OH:5])[OH:2]

Participants

3

Procedure

(1S)-2,3,4,6-Tetra-0-acetyl-1,5-anhydro-1-[5-(1-benzothiophene-2-ylmethyl)-2-(cyclopentyloxy)phenyl]-D-glucitol (381 mg) was dissolved in methanol (10 ml). Sodium methoxide (32 mg) was added to the solution, and the mixture was stirred for three hours at room temperature. The reaction mixture was neutralized with acid ion-exchange resin, and the resin was separated by filtration. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[5-(1-benzothiene-2-yl)methyl]-2-(cyclopentyloxy)phenyl]-D-glucitol (215 mg).

Workup

  1. customthe resin was separated by filtration
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-6f8bb8db102140adbc38ffc3ab2bbbd1
Source dataset
uspto-grants-2007_04
Patent number
US07202350B2

Reaction notes

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