1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-4-(hydroxyamino)-2(1H)-pyrimidinone -Drug Synthesis Database

【结构式】

【分子编号】64249

【品名】1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-4-(hydroxyamino)-2(1H)-pyrimidinone

【CA登记号】

【分子式】C₃₁H₃₁N₃O₆

【分子量】541.60376

【元素组成】C 68.75% H 5.77% N 7.76% O 17.72%

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：(IV)

Treatment of 2',3'-O-isopropylidene-5'-O-trityluridine (I) with 2,4,6-triisopropylbenzenesulfonyl chloride (II) in the presence of DMAP affords the sulfonic ester derivative (III). Subsequent displacement of sulfonate (III) with hydroxylamine leads to the protected N-hydroxycytidine (IV). The protecting groups of (IV) are finally removed with aqueous trifluoroacetic acid to furnish the title compound.

参考文献中间体

合成目标

【1】 Watanabe, K.A.; Stuyver, L. (Pharmasset, Inc.); Modified nucleosides for treatment of viral infections and abnormal cellular proliferation. WO 0232920 .

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)	64247	1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-2,4(1H,3H)-pyrimidinedione		C₃₁H₃₀N₂O₆	详情	详情
(II)	14545	2,4,6-triisopropylbenzenesulfonyl chloride	6553-96-4	C₁₅H₂₃ClO₂S	详情	详情
(III)	64248	1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-2-oxo-1,2-dihydro-4-pyrimidinyl 2,4,6-triisopropylbenzenesulfonate		C₄₆H₅₂N₂O₈S	详情	详情
(IV)	64249	1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-4-(hydroxyamino)-2(1H)-pyrimidinone		C₃₁H₃₁N₃O₆	详情	详情

Extended Information