Azobisisobutyronitrile → 3'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-C-Allylthymidine

HRID 1955834Notes

Reaction equation

[Si:1]([O:18][C@@H:19]1[C@@H:23]([CH2:24]I)[O:22][C@@H:21]([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][C:36](N=NC(C#N)(C)C)(C#N)[CH3:37]>C1(C)C=CC=CC=1>[Si:1]([O:18][C@@H:19]1[C@@H:23]([CH2:24][CH2:37][CH:36]=[CH2:35])[O:22][C@@H:21]([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A stirred solution of 3'-O-(t-butyldiphenylsilyl)-5'-deoxy-5'-iododthymidine (12, 1.77 g, 3 mmol), allytributyltin (2.97 g, 9 mmol) and AIBN (0.54 g, 3.3 mmol) in dry toluene (30 ml) was degassed completely and heated at 65° C. for 6 hr. The solution was cooled and concentrated under vacuo. The residue was purified by silica gel column chromatography and on elution with hexanes:EtOAc (1:1, v/v) furnished the title compound as homogeneous material. Appropriate fractions were pooled and evaporated to furnish 46, 0.75 g of a white foam, 50% yield. The structure was confirmed by 1H NMR.

Workup

temperatureThe solution was cooled
concentrationconcentrated under vacuo
customThe residue was purified by silica gel column chromatography and on elution with hexanes:EtOAc (1:1

Sources & evidence

ORD record: ord-43b4f9dea03b4dcbb624790e1ced8a4d
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05777092

Reaction notes

Loading…