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

HRID 381692

反応式

HRID 381692 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 103342932'-Deoxy-2'-methylthio-5-methyluridine収率 74.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6b367e86d8654ac4a8f7118bd2a4d660
出典データセット
uspto-grants-2001_10
特許番号
US06307040B1

関連ノート

読み込み中…