Trifluoromethanesulfonic acid → 2',3',5'-tri-O-benzoyl-2-chloroadenosine

HRID 241242

반응식

HRID 241242 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.FC(F)(F)C(=N[Si](C)(C)C)O[Si](C)(C)C.S(O)(C(F)(F)F)(=O)=O.C(O[C@@H:39]1[O:61][C@H:60]([CH2:62][O:63][C:64](=[O:71])[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C@@H:50]([O:51][C:52](=[O:59])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C@H:40]1[O:41][C:42](=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=O)C>CC(OC)(C)C.CC#N>[C:42]([O:41][C@@H:40]1[C@H:50]([O:51][C:52](=[O:59])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C@@H:60]([CH2:62][O:63][C:64](=[O:71])[C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)[O:61][C@H:39]1[N:8]1[C:9]2[N:10]=[C:2]([Cl:1])[N:3]=[C:4]([NH2:11])[C:5]=2[N:6]=[CH:7]1)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

참가 물질

7

반응물 4

HCID 62406Trifluoromethanesulfonic acidHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 94358Bis(trimethylsilyl)trifluoroacetamideHCID 949042-Chloroadenine

생성물 1

HCID 866609092',3',5'-tri-O-benzoyl-2-chloroadenosine

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
27.5 °C

실험 절차

Under an atmosphere of N2(g), 2-chloroadenine (A (9), 50 g, 294.9 mmol), MeCN (600 mL), and BSTFA (227.5 g, 883.8 mmol) were stirred and heated under reflux until the mixture turned mostly clear (about 1 h). TfOH (8.77 g, 58.5 mmol) and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (C, 142.5 g, 282.5 mmol) were sequentially added into the mixture and were stirred at reflux for about 1 h. The mixture was cooled to 20-35° C. and diluted with MTBE (500 mL), and washed over a 0.5 to 1 h period with saturated NaHCO3 (750 mL). The organic phase was evaporated in vacuo at 40 to 50° C. to give 2′,3′,5′-tri-O-benzoyl-2-chloroadenosine (D): 1H NMR (300 MHz, CDCl3) δ 7.9-8.1 (m, 6H), 7.94 (s, 1H), 7.3-7.6 (m, 9H), 6.45 (d, J=2.7 Hz 1H), 6.15 (m, 2H), 5.30 (s, 2H), 4.90 (dd, J4′,5a=3.2 Hz, J5′a,5′b=12.0 Hz, 1H), 4.82 (m, 1H), 4.72 (dd, J4′,5a=4.1 Hz, J5′a,5′b=12.0 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ 166.3, 165.5, 165.4, 156.4, 154.7, 151.1, 139.1, 134.1, 134.1, 133.8, 130.2, 130.1, 129.9, 129.4, 129.0, 128.8, 128.5, 119.1, 86.5, 81.3, 74.6, 71.7, 64.0.

후처리

  1. temperatureheated
  2. temperatureunder reflux until the mixture
  3. custom(about 1 h)
  4. temperatureat reflux for about 1 h
  5. washwashed over a 0.5 to 1 h period with saturated NaHCO3 (750 mL)
  6. customThe organic phase was evaporated in vacuo at 40 to 50° C.

출처 및 근거

ORD 기록
ord-7803c2d858fd499abb707eaf12a975e1
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648188B2

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