Benzene → HCID 67143122, compound

HRID 1836218Notes

Reaction equation

HRID 1836218 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@H:22]([O:34][CH2:35][CH2:36][O:37][CH3:38])[C@@H:21]1OC(OC1C=CC=C(C(C)(C)C)C=1)=S)([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.[CH3:53][C:54](N=NC(C#N)(C)C)(C#N)C.[CH:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>>[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@H:22]([O:34][CH2:35][CH2:36][O:37][CH3:38])[C@@H:21]1[CH:53]=[CH:54][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 6547Azobisisobutyronitrile2×HCID 10700230HCID 10700230, compound

Product 1

HCID 67143122HCID 67143122, compound

Conditions

Temperature
40 °C

Procedure

To a solution of 5′-O-(tert-butyldiphenylsilyl)-3′-O-(3-tert-butylphenoxythiocarbonyl)-2′-O-(2-methoxyethyl)-5-methyluridine (15.0 g, 20.0 mmol) in 150 mL of benzene was added PhCH=CHSnBu3 (18.7 g, 50 mmol). The resulting solution was degassed three times with argon at rt and 45° C. After AIBN (1.0 g, 6.1 mmol) was added, the resulting solution was refluxed for 2 h. Another portion of AIBN (1.0 g, 6.1 mmol) was added after cooling to about 40° C. and refluxed for 2 h. This procedure was repeated until the starting material disappeared. The solvent was evaporated and the residue was purified by flash chromatography on a silica gel column using 10:1 and 5:1 hexanes-EtOAc as eluent to give 1.74 g of 5′-O-(tert-butyldiphenylsilyl)-3′-deoxy-2′-O-(2-methoxyethyl)-3′-(2-phenylethenyl)5-methyluridine as a white foam.

Workup

  1. customThe resulting solution was degassed three times with argon at rt
  2. custom45° C
  3. temperaturethe resulting solution was refluxed for 2 h
  4. temperaturerefluxed for 2 h
  5. customThe solvent was evaporated
  6. customthe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-6fdab42ccae54e85995203791c7f7d97
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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