Pyridine → 2'-Deoxy-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}cytidine

HRID 493406

반응식

HRID 493406 반응식
Cl.[C@@H:2]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1.C[Si](C)(C)Cl.[C:23]1([CH2:36][O:37][C:38](Cl)=[O:39])[C:35]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=CC=1.N1C=CC=[CH:43][CH:42]=1>>[C:38]([NH:15][C:14]1[CH:16]=[CH:17][N:10]([C@@H:2]2[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]2)[C:11](=[O:12])[N:13]=1)([O:37][CH2:36][CH:23]1[C:35]2[C:34](=[CH:42][CH:43]=[CH:26][CH:27]=2)[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:39]

참가 물질

5

반응물 4

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 107488Deoxycytidine hydrochlorideHCID 14261773Fluorenylmethyl chloroformate

생성물 1

HCID 143099962'-Deoxy-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}cytidine수율 97%

실험 절차

In one embodiment, 5′-O-DMTR-N4-FMOC-2′-deoxycytidine was prepared according to the following protocol. 30 g (37.9 mmol) of 2′-deoxycytidine hydrochloride were silylated with trimethylchlorosilane (75 ml) in pyridine(160 ml), followed by treatment with fluorenylmethoxycarbonyl chloride (33 g, 128 mmol). After hydrolysis with H2O (300 ml) and extraction with AcOEt/H2O, the N4-FMOC-2′-deoxycytidine was obtained in a 97% yield (49.5 g) as a colorless powder.

후처리

  1. customAfter hydrolysis
  2. extractionwith H2O (300 ml) and extraction with AcOEt/H2O

출처 및 근거

ORD 기록
ord-1b2549656a6349508cf1de1480512213
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534872B2

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