[(2R,3S,4S,5S)-3,4-bis(benzoyloxy)-5-bromotetrahydro-2-thiophenyl]methyl benzoate -Drug Synthesis Database

【结构式】

【分子编号】29616

【品名】[(2R,3S,4S,5S)-3,4-bis(benzoyloxy)-5-bromotetrahydro-2-thiophenyl]methyl benzoate

【CA登记号】

【分子式】C₂₆H₂₁BrO₆S

【分子量】541.41914

【元素组成】C 57.68% H 3.91% Br 14.76% O 17.73% S 5.92%

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：(III)

Methyl 4-thio-beta-D-arabinofuranoside (I) was converted to the tribenzoate ester (II) by means of benzoyl chloride and pyridine, and then treated with HBr in AcOH to give the arabinofuranosyl bromide (III). Displacement of bromide ion in (III) by bis(trimethylsilyl)-N-acetylcytosine (IV) at 130 C led to an anomeric mixture of nucleosides from which the required beta-anomer (V) was isolated by chromatography. Finally, deprotection of the benzoate esters and acetamido group of (V) was performed with methanolic ammonia at 0 C.

参考文献中间体

合成目标

【1】 Whistler, R.L.; et al.; 4-Thio-D-arabinofuranosylpyrimidine nucleosides. J Org Chem 1971, 36, 1, 108.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	29614	(2R,3S,4S,5R)-2-(hydroxymethyl)-5-methoxytetrahydro-3,4-thiophenediol	C₆H₁₂O₄S	详情	详情
(II)	29615	[(2R,3S,4S,5R)-3,4-bis(benzoyloxy)-5-methoxytetrahydro-2-thiophenyl]methyl benzoate	C₂₇H₂₄O₇S	详情	详情
(III)	29616	[(2R,3S,4S,5S)-3,4-bis(benzoyloxy)-5-bromotetrahydro-2-thiophenyl]methyl benzoate	C₂₆H₂₁BrO₆S	详情	详情
(IV)	29617	N-(trimethylsilyl)-N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]acetamide	C₁₂H₂₃N₃O₂Si₂	详情	详情
(V)	29618	[(2R,3S,4S,5R)-5-[4-(acetamido)-2-oxo-1(2H)-pyrimidinyl]-3,4-bis(benzoyloxy)tetrahydro-2-thiophenyl]methyl benzoate	C₃₂H₂₇N₃O₈S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

In a related procedure, arabinofuranosyl bromide (III) was condensed with bis(trimethylsilyl)uracil (VI) to afford, after chromatographic separation, the beta-nucleoside (VII). Subsequent treatment of (VII) with P2S5 produced the 4-thiouridine analogue (VIII). Then, treatment of this derivative with methanolic ammonia at 110 C in a sealed tube yielded the title arabinofuranosyl citosine.

参考文献中间体

合成目标

【1】 Whistler, R.L.; et al.; 4-Thio-D-arabinofuranosylpyrimidine nucleosides. J Org Chem 1971, 36, 1, 108.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(III)	29616	[(2R,3S,4S,5S)-3,4-bis(benzoyloxy)-5-bromotetrahydro-2-thiophenyl]methyl benzoate	C₂₆H₂₁BrO₆S	详情	详情
(VI)	29619	2,4-bis[(trimethylsilyl)oxy]pyrimidine; trimethylsilyl 2-[(trimethylsilyl)oxy]-4-pyrimidinyl ether	C₁₀H₂₀N₂O₂Si₂	详情	详情
(VII)	29620	(2R,3S,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-2-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-thiophenyl benzoate	C₃₀H₂₄N₂O₈S	详情	详情
(VIII)	29621	[(2R,3S,4S,5R)-3,4-bis(benzoyloxy)-5-[2-oxo-4-thioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-thiophenyl]methyl benzoate	C₃₀H₂₄N₂O₇S₂	详情	详情

Extended Information