1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → 6-O-(4,4'-dimethoxytrityl)-2-deoxy-2(thymin-1yl]-3-O-(2-fluoroethyl)D-altro-hexitol

HRID 43299노트

반응식

HRID 43299 반응식
[N:1]1([C@@H:10]([C@@H:13]([C@@H:18]([C@@H:20]([CH2:22][OH:23])[OH:21])[OH:19])[O:14][CH2:15][CH2:16][F:17])[CH2:11][OH:12])[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH3:24][O:25][C:26]1[CH:47]=[CH:46][C:29]([C:30](Cl)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:28][CH:27]=1>>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([C:30]([O:23][CH2:22][C@@H:20]([OH:21])[C@@H:18]([OH:19])[C@@H:13]([O:14][CH2:15][CH2:16][F:17])[C@H:10]([N:1]2[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH2:11][OH:12])([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:29]2[CH:46]=[CH:47][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[CH:36][CH:35]=1

참가 물질

3

반응물 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 866614452-deoxy-2-(thymin-1yl)-3-O-(2-fluoroethyl)-D-altro-hexitol

생성물 1

HCID 866614446-O-(4,4'-dimethoxytrityl)-2-deoxy-2(thymin-1yl]-3-O-(2-fluoroethyl)D-altro-hexitol수율 89%

실험 절차

Compound 5 (4.07 g, 12.79 mmol) was mixed with 4,4′-dimethoxytrityl chloride (4.56 g, 13.46 mmol) and dried over P2O5 under reduced pressure. The residue was dissolved in anhydrous pyridine (43 mL) and stirred at room temperature for 6 hours under an atmosphere of argon. The mixture was quenched with methanol (3 mL). The reaction mixture was diluted with EtOAc (200 mL), washed with aqueous NaHCO3 (saturated, 300 mL) and brine (200 mL) then dried over Na2SO4, filtered and concentrated. The residue obtained was purified by silica gel column chromatography (eluted first with 70% EtOAc in hexanes and then increasing the polarity) to yield Compound 6 (7.1 g, 89%). ES MS m/z 643.2 [M+Na]+.

후처리

  1. dry with materialdried over P2O5 under reduced pressure
  2. dissolutionThe residue was dissolved in anhydrous pyridine (43 mL)
  3. customThe mixture was quenched with methanol (3 mL)
  4. additionThe reaction mixture was diluted with EtOAc (200 mL)
  5. washwashed with aqueous NaHCO3 (saturated, 300 mL) and brine (200 mL)
  6. dry with materialthen dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography (
  11. washeluted first with 70% EtOAc in hexanes
  12. temperatureincreasing the polarity)

출처 및 근거

ORD 기록
ord-99749642d8f449818cfcf864ee94ddd9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536320B2

반응 노트

불러오는 중…