[(2R,3R,4S,5S)-3-(acetoxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate -Drug Synthesis Database

【结构式】

【分子编号】29116

【品名】[(2R,3R,4S,5S)-3-(acetoxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate

【CA登记号】

【分子式】C₁₄H₁₄BrFO₅

【分子量】361.1645632

【元素组成】C 46.56% H 3.91% Br 22.12% F 5.26% O 22.15%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The reaction of 3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (I) with tris(trimethylsilyl)cytosine (II) in methylene chloride gives 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (III), which is hydrolyzed by treatment with methanol NH3 to afford 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (IV). Finally, this compound is iodinated by treatment with HIO3 - I2 in CCl4 - H2O - acetic acid.

参考文献中间体

合成目标

【1】 Lopez, C.; Reichman, U.; Fox, J.; Hirota, K.; Watanabe, K.A.; Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides. J Med Chem 1979, 22, 1, 21-24.
【2】 Thorpe, P.J.; Castaner, J.; FIAC. Drugs Fut 1981, 6, 7, 410.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	29116	[(2R,3R,4S,5S)-3-(acetoxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate	C₁₄H₁₄BrFO₅	详情	详情
(II)	37571	4-[bis(trimethylsilyl)amino]-1-(trimethylsilyl)-2(1H)-pyrimidinone	C₁₃H₂₉N₃OSi₃	详情	详情
(III)	37572	[(2R,3R,4S,5R)-3-(acetoxy)-5-[4-amino-2-oxo-1(2H)-pyrimidinyl]-4-fluorotetrahydro-2-furanyl]methyl benzoate	C₁₈H₁₈FN₃O₆	详情	详情
(IV)	37573	4-amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone	C₉H₁₂FN₃O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

FMAU is prepared by condensation of 3-O-benzoyl-2-fluoro-D-arabinosyl bromide (I) with trimethylsilylated thymine (II) followed by saponification of the protected nucleoside (III).

参考文献中间体

合成目标

【1】 Lopez, C.; Reichman, U.; Fox, J.; Hirota, K.; Watanabe, K.A.; Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides. J Med Chem 1979, 22, 1, 21-24.
【2】 Lopez, C.; Klein, R.S.; Su, T.L.; Fox, J.J.; Watanabe, K.A.; Matsuda, A.; Chun, M.W.; Chun, C.K.; Nucleosides. 123. Synthesis of sntiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-beta-D-arabinofuranosyl)cytosines and -uracils. Some structure-activity relationships. J Med Chem 1983, 28, 2, 152-156.
【3】 Lopez, C.; FMAU. Drugs Fut 1985, 10, 4, 288.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	29116	[(2R,3R,4S,5S)-3-(acetoxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate	C₁₄H₁₄BrFO₅	详情	详情
(II)	12218	5-Methyl-2,4-bis[(trimethylsilyl)methyl]pyrimidine	C₁₃H₂₆N₂Si₂	详情	详情
(III)	29117	[(2R,3R,4S,5R)-3-(acetoxy)-4-fluoro-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate	C₁₉H₁₉FN₂O₇	详情	详情

Extended Information