(3aR,4R)-4-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydrofuro[3,4-d][1,3]dioxol-2-one -Drug Synthesis Database

【结构式】

【分子编号】50021

【品名】(3aR,4R)-4-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydrofuro[3,4-d][1,3]dioxol-2-one

【CA登记号】

【分子式】C₂₇H₂₆O₇

【分子量】462.49924

【元素组成】C 70.12% H 5.67% O 24.22%

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：(I)

The condensation of the cyclic sulfite (I) with N6-benzoyladenine (II) gives the isoadenosine (III), which is condensed with 2-chlorophenylphosphono-bis-triazolide (ClPTr) to yield the phosphate diester (IV). The condensation of (IV) with the deoxycytidine (V) by means of triisopropylbenzenesulfonyl tetrazolide (TPS-TAZ) affords the phosphoric ester (VI), which is treated with dichloroacetic acid (Cl2HOAc) in order to eliminate the dimethoxytrityl protecting group and provide the hydroxymethyl derivative (VII). The phosphorylation of (VII) by means of 2-cyanoethyl phosphate (VIII) gives the protected intermediate (IX), which is finally treated with hot NH4OH to yield the target bis nucleoside phosphate.

参考文献中间体

合成目标

【1】 Taktakishvili, M.; Nair, V.; Pal, s.; Neamati, N.; Pommier, Y.; Recognition and inhibition of HIV integrase by novel dinucleotides. J Am Chem Soc 2000, 122, 24, 5671.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	50021	(3aR,4R)-4-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydrofuro[3,4-d][1,3]dioxol-2-one		C₂₇H₂₆O₇	详情	详情
(II)	10035	N-(9H-Purin-6-yl)benzamide; N6-Benzoyladenine	4005-49-6	C₁₂H₉N₅O	详情	详情
(III)	46816	N-[9-((3R,4S,5R)-5-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]-4-hydroxytetrahydro-3-furanyl)-9H-purin-6-yl]benzamide		C₃₈H₃₅N₅O₆	详情	详情
(IV)	46817	sodium [((2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydro-3-furanyl)oxy](2-chlorophenoxy)oxophosphoranolate		C₄₄H₃₈ClN₅NaO₉P	详情	详情
(V)	46818	(2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-(hydroxymethyl)tetrahydro-3-furanyl acetate		C₁₈H₁₉N₃O₆	详情	详情
(VI)	46819	(2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[[((2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[[bis(4-methoxyphenyl)(phenyl)methoxy]methyl]tetrahydro-3-furanyl)oxy](2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate		C₆₂H₅₆ClN₈O₁₄P	详情	详情
(VII)	46820	(2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[[[(2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-(hydroxymethyl)tetrahydro-3-furanyl]oxy](2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate		C₄₁H₃₈ClN₈O₁₂P	详情	详情
(VIII)	50022	2-cyanoethyl dihydrogen phosphate		C₃H₆NO₄P	详情	详情
(IX)	50023	(2R,3S,5R)-5-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-2-([[([(2R,3S,4R)-4-[6-(benzoylamino)-9H-purin-9-yl]-2-[(phosphonooxy)methyl]tetrahydro-3-furanyl]oxy)(2-chlorophenoxy)phosphoryl]oxy]methyl)tetrahydro-3-furanyl acetate		C₄₁H₃₉ClN₈O₁₅P₂	详情	详情

Extended Information