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

HRID 1600147ノート

反応式

HRID 1600147 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47e9fcdbb80d4ca991d868a5643e4e73
出典データセット
uspto-grants-1998_04
特許番号
US05744465

反応ノート

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