{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】62192

【品名】{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl methanesulfonate

【CA登记号】

【分子式】C₁₁H₁₆N₂O₇S

【分子量】320.32332

【元素组成】C 41.25% H 5.03% N 8.75% O 34.96% S 10.01%

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：(II)

The reaction of 3'-deoxythymidine (I) with MsCl and TEA in acetone gives the mesylate (II), which is treated with aq. NaOH at 45-50 C to yield the anhydro compound (III). Finally, this compound is treated with KOH in refluxing tert-butanol to afford the target Stavudine.

参考文献中间体

合成目标

【1】 Paramashivappa, R.; et al.; Simple and efficient method for the synthesis of 2',3'-didehydro-3'-deoxythymidine (d4T). Tetrahedron Lett 2003, 44, 5, 1003.

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)	12161	Thymidine; 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione	50-89-5	C₁₀H₁₄N₂O₅	详情	详情
(II)	62192	{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl methanesulfonate		C₁₁H₁₆N₂O₇S	详情	详情
(III)	12192	1-[(1R,3R,5R)-2,6-Dioxabicyclo[3.2.0]hept-3-yl]-5-methyl-2,4(1H,3H)-pyrimidinedione		C₁₀H₁₂N₂O₄	详情	详情

Extended Information