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

HRID 493406

反応式

HRID 493406 の反応式
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]

参加物

5

反応物 4

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 107488Deoxycytidine hydrochlorideHCID 14261773Fluorenylmethyl chloroformate

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-1b2549656a6349508cf1de1480512213
出典データセット
uspto-grants-2009_05
特許番号
US07534872B2

関連ノート

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