(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 2252712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2252712
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

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-29c5da51d97248b08d823d229447a512
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323453B2

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