Water → 1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol

HRID 1290438Notes

Reaction equation

HRID 1290438 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C@H:11]2[CH2:17][O:16][C@@H:13]([CH:14]=[O:15])[C@@H:12]2[OH:18])=[CH:5][CH:4]=1.[BH4-].[Na+].O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C@@H:11]2[C@@H:12]([OH:18])[C@H:13]([CH2:14][OH:15])[O:16][CH2:17]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 883373162,5-Anhydro-4-S-[(4-methoxyphenyl)methyl]-4-thio-L-lyxose

Product 1

HCID 676483351,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitolYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a room temperature solution, under argon, of 10.9 g of product from Example 322 in 115 ml of absolute ethyl alcohol is added 1.57 g of sodium borohydride. The reaction is stirred at room temperature for 1 hour. Water is added dropwise with stirring and the mixture is concentrated in vacuo. The residue is extracted with methylene chloride, washed with water, dried and concentrated in vacuo to give after chromatography (Silica gel: 50-75% ethyl acetate/hexane) 7.68 g of the desired product.

Workup

  1. stirringwith stirring
  2. concentrationthe mixture is concentrated in vacuo
  3. extractionThe residue is extracted with methylene chloride
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8869b22427ca4544bb192b038478334d
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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