Methanethiol → 2'-Deoxy-2'-methylthio-5-methyluridine

HRID 381692

반응식

HRID 381692 반응식
[CH3:1][C:2]1[C:16](=[O:17])[N:15]=[C:14]2[N:4]([C@@H:5]3[O:9][C@H:8]([CH2:10][OH:11])[C@@H:7]([OH:12])[C@@H:6]3[O:13]2)[CH:3]=1.[CH3:18][SH:19].CN(C)C(N(C)C)=N>CN(C)C=O>[CH3:18][S:19][C@@H:6]1[C@H:7]([OH:12])[C@@H:8]([CH2:10][OH:11])[O:9][C@H:5]1[N:4]1[CH:3]=[C:2]([CH3:1])[C:16](=[O:17])[NH:15][C:14]1=[O:13]

참가 물질

5

반응물 3

HCID 878MethanethiolHCID 664601,1,3,3-TetramethylguanidineHCID 1680452,2'-Anhydro-1-beta-arabinofuranosylthymine

생성물 1

HCID 103342932'-Deoxy-2'-methylthio-5-methyluridine수율 74.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2.2′-Anhydro-5-methyluridine (17.02 g, 70.6 mmol), methanethiol (16.3 g, 339 mmol), 1,1,3,3-tetramethylguanidine (40.6 g, 353 mmol), and dimethylformamide (150 ml) were heated together at 60° C. After 12 hr, the products were cooled and concentrated under reduced pressure. The residual oil was purified by short silica gel (300 g) column chromatography. Concentration of appropriate fractions, which were eluted with CH2Cl2-MeOH (93:7, v/v), furnished the title compound as a white foam (15.08 g, 74.1%). Crystallization from EtOH-CH2Cl2 furnished white needles.

후처리

  1. temperaturethe products were cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residual oil was purified by short silica gel (300 g) column chromatography
  4. washConcentration of appropriate fractions, which were eluted with CH2Cl2-MeOH (93:7

출처 및 근거

ORD 기록
ord-6b367e86d8654ac4a8f7118bd2a4d660
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307040B1

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