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

HRID 722762

反応式

HRID 722762 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=O)C>[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 DMF (150 mL) were heated at 60° C. After 12 hours, the products were cooled and concentrated under reduced pressure. The residual oil was purified by short silica gel column chromatography (300 g). Pooling and concentrating appropriate fractions, which were eluted with CH2Cl2—MeOH (93:7), furnished the title compound as a white foam (15.08 g, 74.1%), which was crystallized from EtOH—CH2Cl2 as 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 column chromatography (300 g)
  4. concentrationPooling and concentrating appropriate fractions, which
  5. washwere eluted with CH2Cl2—MeOH (93:7)

出典と根拠

ORDレコード
ord-93e2a9d0dda34df689dc139f3bb2a8c9
出典データセット
uspto-grants-2006_11
特許番号
US07138517B2

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