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

HRID 1600147Notes

Reaction equation

HRID 1600147 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+]>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

4

Reactant 2

HCID 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. Wateris added dropwise with stirring and the mixture is concentrated in vacuo. The residue is extracted with methylene chloride, washed with water, driedand concentrated in vacuo to give after chromatography (Silica gel: 50-75% ethyl acetate/hexane) 7.68 g of the desired product.

Workup

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

Sources & evidence

ORD record
ord-47e9fcdbb80d4ca991d868a5643e4e73
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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