[(1S,2R,4R,5S)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methyl methanesulfonate | 183236-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: [(1S,2R,4R,5S)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methyl methanesulfonate
• CAS: 183236-66-0
• 化学式: C₁₁H₁₄N₂O₇S
• 分子量: 318.307
• InChiKey: ISQFRWZDAZYIEO-CHIQAWFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1S,2R,4R,5S)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methyl methanesulfonate 在 铜 、 正丁胺 、 乙酰氯 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 司他夫定
  参考文献：
  名称：

  通过区域/立体控制的β-消除溴乙酸盐来合成抗艾滋病药物d4T的新型无胸腺嘧啶

  摘要：

  The anti-AIDS drug d4T was prepared without contamination of the nucleoside bond cleaved by-product thymine from the readily available ribonucleoside 5-methyluridine (1). This was accomplished by using a new strategy which involved a regio/stereo controlled beta-elimination of trans-bromoacetates 6. (C) 1998 Bristol-Myers Squibb Company. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01084-8
• 作为产物：
  描述：

  5-甲基尿甙 在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 生成 [(1S,2R,4R,5S)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methyl methanesulfonate
  参考文献：
  名称：

  通过区域/立体控制的β-消除溴乙酸盐来合成抗艾滋病药物d4T的新型无胸腺嘧啶

  摘要：

  The anti-AIDS drug d4T was prepared without contamination of the nucleoside bond cleaved by-product thymine from the readily available ribonucleoside 5-methyluridine (1). This was accomplished by using a new strategy which involved a regio/stereo controlled beta-elimination of trans-bromoacetates 6. (C) 1998 Bristol-Myers Squibb Company. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01084-8

文献信息

• A new thymine free synthesis of the anti-AIDS drug d4T via regio/stereo controlled β-elimination of bromoacetates
  作者：Bang-Chi Chen、Sandra L. Quinlan、J. Gregory Reid、Richard H. Spector

  DOI：10.1016/s0040-4039(97)01084-8

  日期：1998.2

  The anti-AIDS drug d4T was prepared without contamination of the nucleoside bond cleaved by-product thymine from the readily available ribonucleoside 5-methyluridine (1). This was accomplished by using a new strategy which involved a regio/stereo controlled beta-elimination of trans-bromoacetates 6. (C) 1998 Bristol-Myers Squibb Company. Published by Elsevier Science Ltd.