Tributylstannane → HCID 9934183, compound

HRID 1682096Notes

Reaction equation

HRID 1682096 reaction equation
C([SnH](CCCC)CCCC)CCC.C(B(CC)CC)C.[Si:21]([O:38][CH2:39][C@H:40]1[O:44][C@@H:43]([N:45]2[CH:53]=[C:51]([CH3:52])[C:49](=[O:50])[NH:48][C:46]2=[O:47])[CH:42]([Se]C2C=CC=CC=2)[CH2:41]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(Cl)Cl.CO>C1C=CC=CC=1.C(#N)C>[Si:21]([O:38][CH2:39][C@H:40]1[O:44][C@@H:43]([N:45]2[CH:53]=[C:51]([CH3:52])[C:49](=[O:50])[NH:48][C:46]2=[O:47])[CH2:42][CH2:41]1)([C:34]([CH3:36])([CH3:35])[CH3:37])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 5948TributylstannaneHCID 7357TriethylboraneHCID 21226129Dichloromethane methanolHCID 86746436HCID 86746436, compound

Product 1

HCID 9934183HCID 9934183, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

Tri-butyltin hydride (0.18 mL, 0.67 mmol), followed by a 1M solution of triethyl borane in hexanes (0.5 mL, 0.5 mmol) were added under argon to a suspension of 5'-O-(t-butyldiphenylsilyl)-3'-deoxy-2'-phenylselenenylthymidine 6 (0.282 g, 0.45 mmol) in anhydrous benzene. The reaction mixture slowly became clear. After 4 hours of stirring, thin layer chromatography (CH2Cl2 /MeOH: 9.5/0.5) indicated complete disappearance of the starting material. The reaction mixture was diluted with acetonitrile then was concentrated to a thick syrup. The syrup was chromatographed through a column of silica gel (230-400 mesh), eluting first with dichloromethane, followed by 3% methanol in dichloromethane. Compound 10 was isolated as a foamy solid. Yield 0.186 g, 89%. 1H NMR (CDCl3, 90 MHz): δ 1.10 (s, 9 H, t-Bu); 1.65 (d, 3 H, 5-CH3, J=1.1 Hz); 1.9-2.4 (m, 4 H, 2' and 3'-H); 3.7-4.3 (m, 3 H, 4' and 5'-H); 6.11 (pseudo t, 1 H, 1'-H, J=4 Hz); 7.26 (s, 1 H, 6-H); 7.4-7.9 (m, 10 H, Ar-H); 8.32 (br s, 1 H, NH). Anal. Calcd for C26H32N2O4 : C, 67.21; H, 6.94; N, 6.03. Found: C, 67.09; H, 6.96; N, 6.01.

Workup

  1. concentrationthen was concentrated to a thick syrup
  2. customThe syrup was chromatographed through a column of silica gel (230-400 mesh)
  3. washeluting first with dichloromethane

Sources & evidence

ORD record
ord-8f70836ba59941d9ab74f5aa6295633c
Source dataset
uspto-grants-1992_12
Patent number
US05175267

Reaction notes

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