2',3'-didehydro-3'-deoxy-5'-O-(methylsulfonyl)thymidine | 140381-05-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2',3'-didehydro-3'-deoxy-5'-O-(methylsulfonyl)thymidine
• 英文别名: [(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl methanesulfonate
• CAS: 140381-05-1
• 化学式: C₁₁H₁₄N₂O₆S
• 分子量: 302.308
• InChiKey: ZDBKDIJKPIGMSD-DTWKUNHWSA-N

物化性质

• 密度：
  1.443±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2',3'-didehydro-3'-deoxy-5'-O-(methylsulfonyl)thymidine 在 正丁胺 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 、 氢溴酸 、 溶剂黄146 、 正丁胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 2',3'-didehydro-3'-deoxy-5'-O-(methylsulfonyl)thymidine
  参考文献：
  名称：

  Independent Synthesis and Fate Studies of Impurities in Process Intermediates of the Anti-AIDS Drug d4T

  摘要：

  Impurities in isolated intermediates in a process to prepare d4T were identified, independently synthesized, and then taken through the process to determine their ultimate fate. Some of the products from these fate studies were also independently synthesized and used in the validation of impurity assay methods.

  DOI：

  10.1021/op970126p

文献信息

• Preparation of D4T from 5-methyluridine
  申请人：Bristol-Myers Squibb Company

  公开号：EP0735044A1

  公开（公告）日：1996-10-02

  The present invention concerns an improved process of making d4T from 5-MU. Another aspect of the invention relates to useful intermediates produced during the process.

  本发明涉及一种从 5-MU 制成 d4T 的改进工艺。本发明的另一方面涉及在该工艺过程中产生的有用中间体。
• Some reactions of (5R)-2-methylene-5-(thymin-1-yl)-2,5-dihydrofuran
  作者：Bhalchandra V. Joshi、Colin B. Reese

  DOI：10.1039/p19920000441

  日期：——

  The title compound 4 was quantitatively converted into the isomeric furan derivative 5 under relatively mild acidic conditions; when compound 4 was treated with 3-chloroperbenzoic acid in dichloromethane and sodium hypochlorite in aqueous dioxane, compounds 9 and 11, respectively, were obtained. Both compounds were isolated in 48% yield.
• US5608049A
  申请人：——

  公开号：US5608049A

  公开（公告）日：1997-03-04
• Independent Synthesis and Fate Studies of Impurities in Process Intermediates of the Anti-AIDS Drug d4T
  作者：Jayachandra P. Reddy、J. Gregory Reid、Deborah A. Renner、Sandra L. Quinlan、Douglas G. Weaver、Bang-Chi Chen、Derron R. Stark、Qi Gao

  DOI：10.1021/op970126p

  日期：1998.5.1

  Impurities in isolated intermediates in a process to prepare d4T were identified, independently synthesized, and then taken through the process to determine their ultimate fate. Some of the products from these fate studies were also independently synthesized and used in the validation of impurity assay methods.
• 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.