(Trimethylsilyl)methyl Trifluoromethanesulfonate [Trimethylsilylmethylating Reagent] → (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-((benzoyloxy)methyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

HRID 2252712Notes

Reaction equation

HRID 2252712 reaction equation
C(O[CH:10]1[O:32][C@H:31]([CH2:33][O:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:21]([O:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@:11]1([CH3:43])[O:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)C1C=CC=CC=1.[NH2:44][C:45]1[N:53]=[C:52]2[C:48]([NH:49][CH:50]=[N:51]2)=[C:47]([Cl:54])[N:46]=1.N12CCCC=C1CCCCN2.FC(F)(F)S(OC[Si](C)(C)C)(=O)=O>C(#N)C>[NH2:44][C:45]1[N:53]=[C:52]2[C:48]([N:49]=[CH:50][N:51]2[C@@H:10]2[O:32][C@H:31]([CH2:33][O:34][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@@H:21]([O:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@:11]2([CH3:43])[O:12][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:47]([Cl:54])[N:46]=1

Participants

6

Reactant 4

HCID 2760857(Trimethylsilyl)methyl Trifluoromethanesulfonate [Trimethylsilylmethylating Reagent]HCID 53603492-Amino-6-chloropurineHCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 11813893D-Ribofuranose, 2-C-methyl-, 1,2,3,5-tetrabenzoate

Product 1

HCID 58730438(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-((benzoyloxy)methyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a pre-cooled solution of 1,2,3,5-tetra-O-benzoyl-2-C-methyl-D-ribofuranose [Harry-O'kuru, Rogers E.; Smith, Jennifer M.; Wolfe, Michael S, “A Short, Flexible Route toward 2′-C-Branched Ribonucleosides,” J. Org. Chem., 62:1754-1759 (1997)] (1.74 g, 3.00 mmol) in acetonitrile (15 mL) was added 2-amino-6-chloropurine (0.56 g, 3.30 mmol), then diazabicyclo[5.4.0]undec-7-ene (DBU) (1.37 g, 9.00 mmol), and then dropwise trimethylsilylmethyl trifluoromethanesulfonate (TMS trifate) (2.67 g, 12.00 mmol). The resulting mixture was heated to 65° C. for 4 h, then cooled and partitioned between saturated aqueous sodium bicarbonate (200 mL) and dichloromethane (200 mL). The organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting crude product was used directly in step B.

Workup

  1. temperaturecooled
  2. custompartitioned between saturated aqueous sodium bicarbonate (200 mL) and dichloromethane (200 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-29c5da51d97248b08d823d229447a512
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

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