N-(9-((2S,3R,4S,5S)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide → 9-(3-O-t-Butyldimethylsilyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-N2-isobutyrylguanine

HRID 1379775Notes

Reaction equation

HRID 1379775 reaction equation
COC1C=CC(C([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:37]=[N:36][C:35]4[C:34](=[O:38])[NH:33][C:32]([NH:39][C:40](=[O:44])[CH:41]([CH3:43])[CH3:42])=[N:31][C:30]3=4)[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](N2C3N=C(NC(=O)C(C)C)NC(=O)C=3N=C2)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:37]=[N:36][C:35]3[C:34](=[O:38])[NH:33][C:32]([NH:39][C:40](=[O:44])[CH:41]([CH3:42])[CH3:43])=[N:31][C:30]2=3)[C@H:26]1[F:45])([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]

Participants

3

Reactant 2

HCID 136395928N-(9-((2S,3R,4S,5S)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramideHCID 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 1372316659-(3-O-t-Butyldimethylsilyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-N2-isobutyrylguanine

Procedure

This compound is prepared from 9-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-β-D-arabinofuranosyl]-N2 -isobutyrylguanine by the same procedure used for the preparation of 3'-O-t-butyldimethylsilyl-N2 -isobutyryl-2'-deoxyguanosine.

Sources & evidence

ORD record
ord-1a8defbc63684dde827937cd4db38615
Source dataset
uspto-grants-1997_09
Patent number
US05672697

Reaction notes

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