Tributylvinyltin → HCID 9840745, compound

HRID 1953070Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH3:14])[O:7][C@H:6]1[N:15]1[CH:22]=[C:21](I)[C:19]([NH2:20])=[N:18][C:16]1=[O:17])(=[O:3])[CH3:2].O1C=C[CH:26]=[C:25]1P(C1OC=CC=1)C1OC=CC=1.C([Sn](CCCC)(CCCC)C=C)CCC>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH3:14])[O:7][C@H:6]1[N:15]1[CH:22]=[C:21]([CH:25]=[CH2:26])[C:19]([NH2:20])=[N:18][C:16]1=[O:17])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2',3'-di-O-acetyl-5'-deoxy-5-iodocytidine (1.6 g, 3.66 mmol) in 10 ml DMF were added Pd2 (dba)3 (67 mg, 0.073 mmol) and tri-2-furylphosphine (85 mg, 0.366 mmol) and tri-n-butyl(vinyl)stannane (2.1 ml, 7.318 mmol ) under Ar atmosphere at room temperature. After stirring for 19 hours, tri-n-butyl(vinyl)stannane (2.1 ml, 7.318 mmol ) was added to the reaction mixture, and then the reaction mixture was warmed up to 40° C. with stirring for 24 hours. The solvent was removed in vacuo, and the residue was purified on a column of silica gel (eluent: ethyl acetate ~CH2Cl2:MeOH=95: 5) to give 2',3'-di-O-acetyl-5'-deoxy-5-vinylcytidine (1.13 g, 92 %) as colorless solid:

Workup

stirringwith stirring for 24 hours
customThe solvent was removed in vacuo
customthe residue was purified on a column of silica gel (eluent: ethyl acetate ~CH2Cl2:MeOH=95: 5)

Sources & evidence

ORD record: ord-4eb86456854e431bb8719d730d7e1936
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06114520

Reaction notes

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