Methanol → Sorbitol

HRID 1012036Notes

Reaction equation

HRID 1012036 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-benzo thiophene-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-benzothien-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-3a5e0055c566420f8b89284d5d48895a
Source dataset
uspto-grants-2011_07
Patent number
US07977466B2

Reaction notes

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