Cytidine, N-benzoyl-2^-deoxy-2^-oxo-3^,5^-O-[1,1,3,3-tetrakis(1-Methylethyl)-1,3-disiloxanediyl]- synthesis

5synthesis methods

Product Name:Cytidine, N-benzoyl-2^-deoxy-2^-oxo-3^,5^-O-[1,1,3,3-tetrakis(1-Methylethyl)-1,3-disiloxanediyl]-
CAS Number:119411-03-9
Molecular formula:C28H41N3O7Si2
Molecular Weight:587.81

N4-Benzoyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine

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Cytidine, N-benzoyl-2^-deoxy-2^-oxo-3^,5^-O-[1,1,3,3-tetrakis(1-Methylethyl)-1,3-disiloxanediyl]-

119411-03-9
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Yield:119411-03-9 84%

Reaction Conditions:

Stage #1: 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N⁴-benzoylcytosinewith dimethyl sulfoxide;trifluoroacetic anhydride in tetrahydrofuran at -20; for 2 h;
Stage #2: with triethylamine in tetrahydrofuran at -15;

Steps:

15.b

Step 15b.; A mixture of the compound from step 15a (56.6 g, 96.0 mmol) and DMSO (44.3 mL, 0.624 mol) in THF (300 mL) was treated with trifluoroacetic anhydride (40.0 ml, 0.288 mol) at -20° C. for 2 hours. Triethylamine (60.2 ml, 0.432 mol) was then added slowly while keeping the internal temperature below -15° C. After addition, the cooling bath was removed and the reaction mixture was allowed to warm up to room temperature before being diluted with ethyl acetate. The organic layer was washed with H₂O (three times), brine, dried (Na₂SO₄), filtered and evaporated. The residue was chromatographed (silica, hexanes-ethyl acetate) to give the desired compound as a yellow foam (47.6 g, 84%). ESIMS m/z=606.21 [M+H+H₂O]⁺.

References:

US2009/274686,2009,A1 Location in patent:Page/Page column 30