ChemicalBook CAS DataBase List N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]cytidine

N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]cytidine synthesis

5synthesis methods

Product Name:N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]cytidine
CAS Number:139434-68-7
Molecular formula:C30H47N3O7SSi2
Molecular Weight:649.95

67-68-5 Synthesis

67-68-5
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N4-Benzoyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)cytidine

69304-43-4
47 suppliers
$45.00/250mg

N-Benzoyl-2'-O-[(methylthio)methyl]-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]cytidine

139434-68-7
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Yield:139434-68-7 80%

Reaction Conditions:

with acetic anhydride;glacial acetic acid at 20;

Steps:

3 4.2.1. Preparation of N-protected-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2′-O-[(methylthio)methyl]nucleosides (2a-d)

General procedure: To a solution of each of N-protected-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-nucleosides (1a-d) in DMSO (45 eq) were added glacial AcOH (52 eq) and Ac2O (24 eq). The reaction mixture was stirred at room temperature for 18-24 h. After the reaction, the resulting solution was poured into sat.NaHCO3 aqueous solution and the mixture was extracted with ethyl acetate. The organic layer was washed with distilled water and brine, and then dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography to afford compounds 2a-d.

References:

Hayashi, Junsuke;Ochi, Yosuke;Morita, Yasuyuki;Soubou, Katsuma;Ohtomo, Yuhei;Nishigaki, Misa;Tochiyama, Yuko;Nakagawa, Osamu;Wada, Shun-ichi;Urata, Hidehito [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 22,p. 5838 - 5844]

79154-57-7 Synthesis