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

HRID 493406Notes

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

Reactant 4

HCID 1049Pyridine

HCID 6397Chlorotrimethylsilane

HCID 107488Deoxycytidine hydrochloride

HCID 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

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

Sources & evidence

ORD record: ord-1b2549656a6349508cf1de1480512213
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534872B2

Reaction notes

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