Trimethylsilyl triflate → Acetic acid 2-(6-benzoylamino-purin-9-yl)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-3-yl ester

HRID 1893159Notes

Reaction equation

HRID 1893159 reaction equation
[C:1]([O:4][CH:5]1[CH:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:21][SiH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])([CH:18]=[CH2:19])[O:7][CH:6]1OC(=O)C)(=[O:3])[CH3:2].O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.[C:55]([NH:63][C:64]1[N:72]=[CH:71][N:70]=[C:69]2[C:65]=1[NH:66][CH:67]=[N:68]2)(=[O:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>C(#N)C>[C:55]([NH:63][C:64]1[N:72]=[CH:71][N:70]=[C:69]2[C:65]=1[N:66]=[CH:67][N:68]2[CH:6]1[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH:9]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:20]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:21][SiH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])([CH:18]=[CH2:19])[O:7]1)(=[O:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 970756-BenzamidopurineHCID 131730809Acetic acid 3-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl ester

Product 1

HCID 131730810Acetic acid 2-(6-benzoylamino-purin-9-yl)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-3-yl esterYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A flask was charged with Acetic acid 3-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl ester, acetonitrile, the trimethylsilyl triflate (TMSOTf). To the reaction was added N6-benzoyl adenine. The reaction was stirred, extracted, and the solvent was evaporated to provide the titled compound in 68% yield.

Workup

  1. extractionextracted
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-63c85fc8b1304f72be5ba0cfdc247b07
Source dataset
uspto-grants-2013_08
Patent number
US08513214B2

Reaction notes

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