N-[1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide → 1-(3-O-t-Butyldimethylsilyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-N4-benzoylcytosine

HRID 1379776Notes

Reaction equation

COC1C=CC(C([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:44]=[CH:43][C:33]([NH:34][C:35](=[O:42])[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[N:32][C:30]3=[O:31])[C@@H:26]([F:45])[C@@H:25]2[OH:46])(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1.[Si:49](O[C@@H]1[C@@H](CO)O[C@@H](N2C=CC(NC(=O)C3C=CC=CC=3)=NC2=O)C1)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]>>[Si:49]([O:46][C@@H:25]1[C@@H:24]([CH2:23][OH:22])[O:28][C@@H:27]([N:29]2[CH:44]=[CH:43][C:33]([NH:34][C:35](=[O:42])[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[N:32][C:30]2=[O:31])[C@H:26]1[F:45])([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]

Participants

Reactant 2

HCID 10647001N-[1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide

HCID 70700565N-(1-((2R,3S,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Product 1

HCID 1317202171-(3-O-t-Butyldimethylsilyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-N4-benzoylcytosine

Procedure

This compound is prepared from 1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-β-D-arabinofuranosyl]-N4 -benzoylcytosine by the same procedure used for the preparation of 3'-O-t-butyldimethylsilyl-N4 -benzoyl-2'-deoxycytidine.

Sources & evidence

ORD record: ord-62b69565f3524e9b968e409cac5fa69d
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05672697

Reaction notes

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