(5R,6R)-1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-bromo-6-methoxy-5-methyldihydro-2,4(1H,3H)-pyrimidinedione -Drug Synthesis Database

【结构式】

【分子编号】25319

【品名】(5R,6R)-1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-bromo-6-methoxy-5-methyldihydro-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【分子式】C₁₁H₁₆BrN₅O₅

【分子量】378.18274

【元素组成】C 34.94% H 4.26% Br 21.13% N 18.52% O 21.15%

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：(VII)

In a related procedure, methyl hypobromite was added to 3'-azidothimidine (V) in MeOH, and the resulting mixture of diastereomeric 5-bromo-6-methoxypyrimidines (VII) and (VIII) was separated by column chromatography. Both the (5R,6R)- and the (5S,6S)-isomers (VII) and (VIII) were then coupled to phosphorochloridate (IV) to yield the title compound as seperated enantiomers.

参考文献中间体

合成目标

【1】 D'Cruz, O.; Jan, S.-T.; Shih, M.-J.; Chen, C.-L.; Uckun, F.M.; Venkatachalam, T.K.; Synthesis of dual function (5R,6R)- and (5S,6S)-5-bromo-6-methoxy-5,6-dihydro-AZT-5'-(para-bromophenyl methoxyalaninyl phosphate) as novel spermicidal and anti-HIV agents. Antivir Chem Chemother 1999, 10, 1, 39.
【2】 Uckun, F.M.; Venkatachalam, T.; D'Cruz, O. (Parker Hughes Institute); AZT derivs. exhibiting spermicidal and anti-viral activity. WO 9948902 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	25316	methyl 2-[[(4-bromophenoxy)(chloro)phosphoryl]amino]propanoate		C₁₀H₁₂BrClNO₄P	详情	详情
(V)	25317	1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione	101703-35-9	C₁₀H₁₃N₅O₄	详情	详情
(VII)	25319	(5R,6R)-1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-bromo-6-methoxy-5-methyldihydro-2,4(1H,3H)-pyrimidinedione		C₁₁H₁₆BrN₅O₅	详情	详情
(VIII)	25320	(5S,6S)-1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-bromo-6-methoxy-5-methyldihydro-2,4(1H,3H)-pyrimidinedione		C₁₁H₁₆BrN₅O₅	详情	详情

Extended Information