(+)-3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)cytidine synthesis
- Product Name:(+)-3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)cytidine
- CAS Number:69304-42-3
- Molecular formula:C21H39N3O6Si2
- Molecular Weight:485.72
Yield: 7.8 g
Reaction Conditions:
with pyridine at 20; for 15.25 h;
Steps:
3.A Step A-Synthesis of Compound Int-3b
Step A-Synthesis of Compound Int-3b [0228] Uridine (Int-3a, 5.0 g, 18.0 mmol) was azeotroped with pyridine (2×15 mL) and then suspended in pyridine (25 mL). Tetraisopropyldisiloxanedichloride (6.06 mL mL, 18.95 mmol) was added dropwise over fifteen minutes and the reaction was allowed to stir for about 15 hours at room temperature. The reaction was diluted with water and extracted with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was azeotroped with toluene (2×50 mL) to provide 7.8 g of compound Int-3b as a white solid that was used without purification. [M+H]=487.42.
References:
MERCK SHARP & DOHME CORP.;Girijavallabhan, Vinay;Njoroge, F. George;Bogen, Stephane;Kerekes, Angela;Bennett, Frank;Huang, Ying;Nair, Latha;Pissarnitski, Dmitri;Verma, Vishal;Dang, Qun;Davies, Ian;Olsen, David B.;Stamford, Andrew;Vacca, Joseph P. US2014/161770, 2014, A1 Location in patent:Paragraph 0228
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