Phenyl isocyanate → HCID 66842590, compound

HRID 889781Notes

Reaction equation

HRID 889781 reaction equation
[C:1]([CH:9]([OH:34])[C@H:10]1[O:14][C@@H:13]([N:15]2[C:31]3[N:30]=[CH:29][N:28]=[C:19]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:18]=3[N:17]=[CH:16]2)[C@H:12]([OH:32])[C@@H:11]1[OH:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[Sn](O[Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC.[C:62]1([N:68]=[C:69]=[O:70])[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>C1(C)C=CC=CC=1.CN(C=O)C>[C:1]([CH:9]([OH:34])[C@H:10]1[O:14][C@@H:13]([N:15]2[C:31]3[N:30]=[CH:29][N:28]=[C:19]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:18]=3[N:17]=[CH:16]2)[C@H:12]([O:32][C:69](=[O:70])[NH:68][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[C@@H:11]1[OH:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([CH:9]([OH:34])[C@H:10]1[O:14][C@@H:13]([N:15]2[C:31]3[N:30]=[CH:29][N:28]=[C:19]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:18]=3[N:17]=[CH:16]2)[C@H:12]([OH:32])[C@@H:11]1[O:33][C:69](=[O:70])[NH:68][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 16682746Bis(tributyltin) oxideHCID 66842737HCID 66842737, compound

Product 2

HCID 66842590HCID 66842590, compoundHCID 66842817HCID 66842817, compound

Reagents, catalysts & solvents 1

HCID 21735183Dimethylformamide tolueneSolvent

Procedure

The toluene-DMF mixed solvent solution of 5′-benzoyl-N6-benzyladenosine (0.1 mmol) and bis(tributyltin) oxide (0.05 mmol) and phenyl isocyanate (0.2 mmol) was stirred at −78° C. to −48° C. for 49 hours, to obtain 5′-benzoyl-N6-benzyl-2′-O-phenylcarbamoyladenosine with the yield of 60% and 5′-benzoyl-N6-benzyl-3′-O-phenylcarbamoyladenosine with the yield of 40%.

Sources & evidence

ORD record
ord-ae6efa2986de42c6ac989d0f2aa229f8
Source dataset
uspto-grants-2012_08
Patent number
US08252919B2

Reaction notes

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