(2R,3R,3aS,9aR)-7-methyl-2-[[(methylsulfonyl)oxy]methyl]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-yl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】41035

【品名】(2R,3R,3aS,9aR)-7-methyl-2-[[(methylsulfonyl)oxy]methyl]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-yl methanesulfonate

【CA登记号】

【分子式】C₁₂H₁₆N₂O₉S₂

【分子量】396.39912

【元素组成】C 36.36% H 4.07% N 7.07% O 36.33% S 16.18%

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)

An improved process for the preparation of high purity stavudine in a good yield was reported: The reaction of 5-methyluridine (I) with mesyl chloride and NMM in acetone, followed by a treatment with 6N NaOH gives the 2,2'-anhydro-5-methyluridine derivative (II), which is treated successively with potassium benzoate in DMF, HBr in acetic acid, and finally with Zn in DMF to yield 2',3'-anhydro-5'-O-benzoylthymidine (III). Finally, this compound is debenzoylated with hot butylamine.

参考文献中间体

合成目标

【1】 Reddy, J.P.; Quinlan, S.L.; Reid, J.G.; Renner, D.A.; Weaver, D.G.; Stark, D.R.; Chen, B.-C.; Independent syntesis and fate studies of impurities in process intermediates of the anti-AIDS drug d4T. Org Process Res Dev 1998, 2, 3, 203.

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)	12206	1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine	1463-10-1	C₁₀H₁₄N₂O₆	详情	详情
(II)	41035	(2R,3R,3aS,9aR)-7-methyl-2-[[(methylsulfonyl)oxy]methyl]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-yl methanesulfonate		C₁₂H₁₆N₂O₉S₂	详情	详情
(III)	12254	[(2S,5R)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl benzoate		C₁₇H₁₆N₂O₅	详情	详情

Extended Information