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

HRID 493406

Reaction equation

HRID 493406 reaction equation
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]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 107488Deoxycytidine hydrochlorideHCID 14261773Fluorenylmethyl chloroformate

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-1b2549656a6349508cf1de1480512213
Source dataset
uspto-grants-2009_05
Patent number
US07534872B2

Linked notes

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