N-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine → N-[1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide

HRID 1379768Notes

Reaction equation

HRID 1379768 reaction equation
[C:1]([NH:9][C:10]1[CH:46]=[CH:45][N:13]([C@@H:14]2[O:44][C@H:18]([CH2:19][O:20]C(C3C=CC=CC=3)(C3C=CC(OC)=CC=3)C3C=CC(OC)=CC=3)[C@@H:16]([OH:17])[CH2:15]2)[C:12](=[O:47])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:48](O[C@@H]1[C@@H](CO)O[C@@H](N2C3N=C(NC(=O)C(C)C)NC(=O)C=3N=C2)C1)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49]>>[Si:48]([O:17][C@@H:16]1[C@@H:18]([CH2:19][OH:20])[O:44][C@@H:14]([N:13]2[CH:45]=[CH:46][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:11][C:12]2=[O:47])[CH2:15]1)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49]

Participants

3

Reactant 2

HCID 2724490N-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidineHCID 136483518N-(9-((2R,4S,5R)-4-((tert-Butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-3H-purin-2-yl)isobutyramide

Product 1

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

Procedure

This compound was prepared from N4 -benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine by the same procedure used for the preparation of 3'-O-t-butyldimethylsilyl-N2 -isobutyryl-2'-deoxyguanosine.

Sources & evidence

ORD record
ord-f240df17c5f44afdb69d502da64626c0
Source dataset
uspto-grants-1997_09
Patent number
US05672697

Reaction notes

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