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

HRID 722762

반응식

HRID 722762 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=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]

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 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-93e2a9d0dda34df689dc139f3bb2a8c9
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138517B2

연결된 노트

불러오는 중…