1-[(6aS,8S,9S,9aR)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methyl-2,4(1H,3H)-pyrimidinedione -Drug Synthesis Database

【结构式】

【分子编号】62920

【品名】1-[(6aS,8S,9S,9aR)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methyl-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【分子式】C₂₂H₄₀N₂O₇Si₂

【分子量】500.73988

【元素组成】C 52.77% H 8.05% N 5.59% O 22.37% Si 11.22%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XXXVIII)

Condensation of 1-(b-L-ribofuranosyl)thymine (XXXVI) with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (XXXVII) in pyridine gives the cyclic disiloxane nucleoside (XXXVIII), which is acylated with thiocarbonyldiimidazole (TCDI) in DMF to yield the 2'-O-thioester derivative (XXXIX). Reduction of this compound by means of 2,2'-azobis(methylpropionitrile) (ABMP) and Bu3SnH in refluxing toluene affords the silylated 2'-deoxynucleoside (XL), which is finally desilylated by means of TBAF in THF.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castañer, J.; Castañer, R.M.; Bayes, M.; Telbivudine. Drugs Fut 2003, 28, 9, 870.
【2】 Dowle, M.D.; Wu, W.-Y.; Jin, B.; Mason, A.M.; McConnell, D.; MacDonald, S.J.F.; Shanahan, S.E.; Nguyen, V.T.T. (Biota Scientific Management Pty Ltd.); Dimeric cpds. and their use as anti-viral agents. WO 0340135 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXXVI)	12206	1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine	1463-10-1	C₁₀H₁₄N₂O₆	详情	详情
(XXXVII)	29242	1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane	69304-37-6	C₁₂H₂₈Cl₂OSi₂	详情	详情
(XXXVIII)	62920	1-[(6aS,8S,9S,9aR)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methyl-2,4(1H,3H)-pyrimidinedione		C₂₂H₄₀N₂O₇Si₂	详情	详情
(XXXIX)	62921	O-{(6aS,8S,9S,9aS)-2,2,4,4-tetraisopropyl-8-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl} 1H-imidazole-1-carbothioate		C₂₆H₄₂N₄O₇SSi₂	详情	详情
(XL)	62922	1-[(6aS,8S,9aR)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methyl-2,4(1H,3H)-pyrimidinedione		C₂₂H₄₀N₂O₆Si₂	详情	详情

Extended Information