Réaction #82914

ord-764afb4f4adc45c882af92922ad7a2cc

Équation de réaction

Cc1cn([C@H]2C[C@H](O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](CI)O2)c(=O)[nH]c1=O
3'-O-(t-butyldiphenylsilyl)-5'-deoxy-5'-iododthymidine
Cc1cn([C@H]2C[C@H](O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](CI)O2)c(=O)[nH]c1=O
3'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-Iodothymidine
CC(C)(C#N)N=NC(C)(C)C#N
AIBN
→
C=CCC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
title compound
C=CCC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
3'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-C-Allylthymidine

Réactifs

Cc1cn([C@H]2C[C@H](O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](CI)O2)c(=O)[nH]c1=O
3'-O-(t-butyldiphenylsilyl)-5'-deoxy-5'-iododthymidine
Cc1cn([C@H]2C[C@H](O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](CI)O2)c(=O)[nH]c1=O
3'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-Iodothymidine
CC(C)(C#N)N=NC(C)(C)C#N
AIBN

Réactifs

Aucun

Solvants

Cc1ccccc1
toluene

Conditions de réaction

Température
65°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureThe solution was cooled
  2. 2
    Concentrationconcentrated under vacuo
  3. 3
    AutreThe residue was purified by silica gel column chromatography and on elution with hexanes:EtOAc (1:1

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05623070uspto-grants-1997_04