2-Dimethylaminopyridine → Thiocarbonic acid O-[2-(6-amino-purin-9-yl)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-3-yl]ester O-phenyl ester

HRID 1893161Notes

Reaction equation

HRID 1893161 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[CH:15]([OH:16])[CH:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:28][SiH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH:25]=[CH2:26])[O:12]1.CN(C1C=CC=CN=1)C.[C:55]1([O:61][C:62](Cl)=[S:63])[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>C(#N)C>[C:55]1([O:61][C:62](=[S:63])[O:16][CH:15]2[CH:14]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:13]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[O:28][SiH2:29][C:30]([CH3:31])([CH3:32])[CH3:33])([CH:25]=[CH2:26])[O:12][CH:11]2[N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[NH2:1])[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 70498Phenyl thioxochloroformateHCID 1317308112-(6-Amino-purin-9-yl)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-3-ol

Product 1

HCID 131730812Thiocarbonic acid O-[2-(6-amino-purin-9-yl)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-3-yl]ester O-phenyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A flask was charged with 2-(6-Amino-purin-9-yl)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-3-ol, acetonitrile, dimethylamino pyridine (DMAP), and PhOCSCl. The reaction was stirred, extracted, and the solvent was evaporated to provide the titled compound in 82% yield.

Workup

  1. extractionextracted
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a0dcc95a44054643b866fc32b430e916
Source dataset
uspto-grants-2013_08
Patent number
US08513214B2

Reaction notes

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