　 -Drug Synthesis Database

【结构式】

【分子编号】47692

【品名】　

【CA登记号】

【分子式】C₄₅H₉₆N₅O₁₅P₃

【分子量】1040.203226

【元素组成】C 51.96% H 9.3% N 6.73% O 23.07% P 8.93%

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：(V)

INS-365 can be obtained by several different ways: 1) Dimerization of uridine-5'-monophosphate tributyl-ammonium salt (I) with bis(triethylammonium) pyrophosphate (II) by means of CDI, followed by purification by semipreparative ionexchange chromatography. 2) Reaction of uridine-5'-diphosphate (III) with CDI in DMF gives the corresponding adduct (IV), which is then condensed with more uridine-5'-diphosphate (III), affording INS-365 which is purified by chromatography as before. 3) Reaction of uridine-5'-triphosphate tributylammonium salt (V) with CDI in DMF gives the cyclic triphosphate (VI), which is then condensed with uridine-5'-monophosphate (I) in hot DMF to provide INS-365 which is purified by chromatography as before.

参考文献中间体

合成目标

【1】 Redick, C.C.; Sims, I.F.; Rideout, J.L.; Shaver, S.R.; Douglass, J.G. III; Pendergast, W.; Yerxa, B.R.; Dougherty, R.W.; Synthesis and P2Y receptor activity of a series of uridine dinucleoside 5'-polyphosphates. Bioorg Med Chem Lett 2001, 11, 2, 157.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	47688		C₂₁H₄₀N₃O₉P	详情	详情
(II)	47689	di(N,N-diethyl-1-ethanaminium) 1,3-dihydroxy-1,3-dioxo-1lambda(5),3lambda(5)-diphosphoxane-1,3-diolate	C₁₂H₃₄N₂O₇P₂	详情	详情
(III)	47690		C₃₃H₆₈N₄O₁₂P₂	详情	详情
(IV)	47691	di(N,N-dibutyl-1-butanaminium) 1-([(2R,3S,4R,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl]methoxy)-3-(1H-imidazol-1-yl)-1,3-dioxo-1lambda(5),3lambda(5)-diphosphoxane-1,3-diolate	C₃₆H₇₀N₆O₁₁P₂	详情	详情
(V)	47692		C₄₅H₉₆N₅O₁₅P₃	详情	详情
(VI)	47693	di(N,N-dibutyl-1-butanaminium) 6-([(2R,3S,4R,5R)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl]methoxy)-2,4,6-trioxo-1,3,5,2lambda(5),4lambda(5),6lambda(5)-trioxatriphosphinane-2,4-diolate	C₃₃H₆₇N₄O₁₄P₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

INS-365 can also been obtained by the following ways: 4) Dimerization of uridine-5'-monophosphate tributyl-ammonium salt (I) with bis(tributylammonium) pyrophosphate (II) by means of CDI, followed by purification by semipreparative ionexchange chromatography. 5) Dimerization of uridine-5'-monophosphate tributyl-ammonium salt (I) with pyrophosphoryl chloride (III) in pyridine, followed by chromatographic purification as before. 6) Condensation of uridine (IV) with POCl3 and bis(tributylammonium) pyrophosphate (II) by means of tributylamine in trimethyl phosphate, followed by chromatographic purification as before. 7) Dimerization of uridine-5'-diphosphate tributylammonium salt (V) by means of CDI in DMF, followed by purification over Dowex 50Wx4 Na+. 8) Condensation of uridine-5'-triphosphate tributylammonium salt (VI) with uridine-5'-monophosphate tributyl-ammonium salt (I) by means of DCC in DMF, followed by chromatographic purification as before. 9) Reaction of uridine-5'-monophosphate tributylammonium salt (I) with CDI in DMF, followed by condensation with uridine-5'-triphosphate (VI) and chromatographic purification as before.

参考文献中间体

合成目标

【1】 Yerxa, B.J.; Pendergast, W. (Inspire Pharmaceuticals, Inc.); Method for large-scale production of di(uridine 5'-tetraphosphate) and salts thereof. JP 2001510484; WO 9905155 .

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)	47688			C₂₁H₄₀N₃O₉P	详情	详情
(II)	47695	di(N,N-dibutyl-1-butanaminium) 1,3-dihydroxy-1,3-dioxo-1lambda(5),3lambda(5)-diphosphoxane-1,3-diolate		C₂₄H₅₈N₂O₇P₂	详情	详情
(III)	47694	Pyrophosphoric tetrachloride		Cl₄O₃P₂	详情	详情
(IV)	11996	1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; Uridine	58-96-8	C₉H₁₂N₂O₆	详情	详情
(V)	47690			C₃₃H₆₈N₄O₁₂P₂	详情	详情
(VI)	47692			C₄₅H₉₆N₅O₁₅P₃	详情	详情

Extended Information