2-Methylbenzenesulfonic acid → HCID 178477164, 화합물

HRID 1600155

반응식

HRID 1600155 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 178477164HCID 178477164, 화합물수율 67.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  1. customflash chromatographed on silica gel

출처 및 근거

ORD 기록
ord-9a47062e05234ee1bbafc129cfa78050
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05744465

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