2-Methylbenzenesulfonic acid → HCID 178477164、化合物

HRID 54829

反応式

HRID 54829 の反応式
[Si:1]([O:18][CH2:19][C@H:20]1[S:25][CH:23]([OH:24])[CH2:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([OH:29])(=S)[CH3:27].C1(C)C(S(O)(=O)=O)=CC=CC=1>C(Cl)Cl>[C:26]([SH:25]1[CH:23]([OH:24])[CH2:22][CH2:21][C@H:20]1[CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:29])[CH3:27]

参加物

5

反応物 3

HCID 69252-Methylbenzenesulfonic acidHCID 542684695-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranoseHCID 178418634HCID 178418634、化合物

生成物 1

HCID 178477164HCID 178477164、化合物収率 67.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Two grams of 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose (prepared according to J. A. Secrist et al., J. Med. Chem., 1992,35,533) is stirred with 0.456 g of thioacetic acid in 25 ml of methylene chloride and 0.0.025 g of toluenesulfonic acid for 68 hours. On workup the reactiion is adsorbed onto magnesium silicate and then flash chromatographed on silica gel to give 1.5 g of the desired product.

後処理

  1. customflash chromatographed on silica gel

出典と根拠

ORDレコード
ord-4157e3b36b154ed298b12651e76816a0
出典データセット
uspto-grants-1997_04
特許番号
US05623081

関連ノート

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