4-Toluenesulfonyl chloride → 1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)

HRID 1290439ノート

反応式

HRID 1290439 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[C@@H:15]([OH:16])[C@H:14]([CH2:17][OH:18])[O:13][CH2:12]2)=[CH:5][CH:4]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:18][CH2:17][C@@H:14]2[O:13][CH2:12][C@H:11]([S:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C@H:15]2[OH:16])(=[O:27])=[O:26])=[CH:21][CH:20]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 676483351,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol

生成物 1

HCID 883371051,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)収率 57.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a 0° C. solution, under argon, of 0.580 g of product from Example 323 in 10 ml of pyridine is added 0.430 g of p-toluenesulfonyl chloride. The reaction is stirred at room temperature overnight. The mixture is quenched with water, extracted with diethyl ether, washed with water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by chromatography (Silica gel: 50% ethyl acetate/hexane) to give 0.520 g of the desired product.

後処理

  1. customThe mixture is quenched with water
  2. extractionextracted with diethyl ether
  3. washwashed with water and saturated sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography (Silica gel: 50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-1c12c551d864427aacf603d06842b36e
出典データセット
uspto-grants-1998_05
特許番号
US05750735

反応ノート

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