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

HRID 1600147노트

반응식

HRID 1600147 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47e9fcdbb80d4ca991d868a5643e4e73
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05744465

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