(2Xi)-3',5'-二-O-乙酰基-2'-溴-2'-脱氧-3,4-二氢胸苷 | 110483-43-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: (2Xi)-3',5'-二-O-乙酰基-2'-溴-2'-脱氧-3,4-二氢胸苷
• 英文名称: 1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine
• 英文别名: 2'-Bromo-2'-deoxy-5-methyluridine 3',5'-diacetate；[(2R,3R,4R,5R)-3-acetyloxy-4-bromo-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 110483-43-7
• 化学式: C₁₄H₁₇BrN₂O₇
• 分子量: 405.202
• InChiKey: LIZACCKAVBPBPQ-PRULPYPASA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2Xi)-3',5'-二-O-乙酰基-2'-溴-2'-脱氧-3,4-二氢胸苷 在 palladium on activated charcoal sodium hydroxide 、 三乙胺 、 氘 作用下， 以 吡啶 为溶剂， 反应 12.0h， 生成 <2'-²H>-3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)thymidine
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxypurinenucleosides via the Palladium Catalyzed Reduction of 9-(2,5-Di-O-acetyl-3-bromo-3-deoxy-β-d-xylofuranosyl)purine Derivatives

  摘要：

  Practical method to produce 2',3'-dideoxypurinenucleosides from 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)purines (1) was developed. High ratio of 2',3 '-dideoxynucleoside to 3'-deoxyribonucleoside was obtained by Selecting the reaction conditions (solvent, pH and/or base), or changing 2'-acyloxy leaving group. The reaction mechanism was studied by deuteration experiments of 1a and 1-(3,5-di-O-acetyl-2-bromo-2-deoxy-beta-D-ribofuranosyl)thymine (12).

  DOI：

  10.1080/07328319608002368
• 作为产物：
  描述：

  1-乙酰基-三-苄氧基-罗伯糖 在 三甲基氯硅烷 、 三氟甲磺酸 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 (2Xi)-3',5'-二-O-乙酰基-2'-溴-2'-脱氧-3,4-二氢胸苷
  参考文献：
  名称：

  Preparation of 1-(2,3-dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)thymine (d4T) and 2',3'-dideoxyadenosine (ddA): general methods for the synthesis of 2',3'-olefinic and 2',3'-dideoxy nucleoside analogs active against HIV

  摘要：

  DOI：

  10.1021/jo00281a017

文献信息

• An Integrated Chemo-enzymatic Route for Preparation of β-Thymidine, a Key Intermediate in the Preparation of Antiretrovirals
  作者：Gregory E. R. Gordon、Moira L. Bode、Daniel F. Visser、M. Jerry Lepuru、Jacob G. Zeevaart、Nasheen Ragubeer、Molala Ratsaka、David R. Walwyn、Dean Brady

  DOI：10.1021/op100208x

  日期：2011.1.21

  A chemo-enzymatic method for production of β-thymidine, an intermediate in the synthesis of antiretrovirals, is described. Guanosine and thymine were converted by means of enzymatic transglycosylation to yield 5-methyluridine (5-MU), which was reproducibly synthesised at a 10−20-L scale in 85% yield at a final product concentration of ∼80 g·L−1. A downstream processing (DSP) protocol was designed to

  描述了产生β-胸苷的化学酶促方法，β-胸苷是抗逆转录病毒药合成中的中间体。鸟苷和胸腺嘧啶通过酶促糖基化作用转化为5-甲基尿苷（5-MU），可再生地以10-20-L的规模合成，产率为85％，最终产物浓度为〜80 g·L -1。设计了下游处理（DSP）方案以去除干扰后续合成步骤的反应组分。发现在生物催化反应中产生的结晶的5-MU的行为与市售的5-MU相似，并且已成功地证明了初始生物催化和随后的三步化学过程与β-胸腺嘧啶核苷的整合。
• SYNTHESIS OF 2′,3′-DIDEOXY-2′,3′-DIDEHYDRO NUCLEOSIDES VIA A SERENDIPITOUS ROUTE
  作者：Z. Guo、Y. S. Sanghvi、L. E. Brammer、T. Hudlicky

  DOI：10.1081/ncn-100002532

  日期：2001.3.31

  This paper describes a "green" synthesis of 2',3'-unsaturated 2',3'-dideoxynucleosides via an electrochemical reaction. Using this approach d4T, d4U, ddA and ddI can be synthesized in high yields.

  本文描述了通过电化学反应“绿色”合成2'，3'-不饱和2'，3'-二脱氧核苷。使用这种方法，可以高收率合成d4T，d4U，ddA和ddI。
• Process for preparing 2',3'-Dideoxy-2',3'-dehydronucleosides
  申请人：Ajinomoto Co., Inc.

  公开号：US05625057A1

  公开（公告）日：1997-04-29

  A process for preparing a 2', 3'-dideoxy-2',3'-didehydropyrimidine nucleoside comprising reacting the pyrimidine ribofuranoside with a trialkyl orthoester to yield the 2',3'-O-alkoxyethylidene derivative; which is reacted with hydrogen bromide in acetic acid or acetyl bromide to yield the 2-deoxy-2'-bromo-3'-acetyl-pyrimidine nucleoside; which is then reduced with zinc to yield the 2',3'-olefin of the pyrimidine nucleoside.

  制备2'，3'-二脱氧-2'，3'-二脱氢嘧啶核苷的过程包括将嘧啶核糖呋喃苷与三烷基正酯反应，得到2'，3'-O-烷氧乙烯基衍生物；然后将其与乙酸中的溴化氢或乙酰溴反应，得到2-脱氧-2'-溴-3'-乙酰-嘧啶核苷；然后用锌还原，得到嘧啶核苷的2'，3'-烯烃。
• Pyrimidine nucleoside derivatives and methods for producing them
  申请人：Ajinomoto Co., Inc.

  公开号：US05633366A1

  公开（公告）日：1997-05-27

  Nucleoside derivatives such as 2'-deoxy-2'-bromo-5'-O-acetyl-5-methyluridine, etc., are important intermediates which can be converted into nucleoside derivatives, such as 3'-azido-3'-deoxythymidine, etc., which are useful as medicines.

  核苷衍生物，如2'-脱氧-2'-溴-5'-O-乙酰-5-甲基尿苷等，是重要的中间体，可以转化为核苷衍生物，如3'-氮杂-3'-脱氧胸苷等，这些对药物具有用处。
• Process for preparing 5′-acetylstavudine
  申请人：Clariant Life Science Molecules (Italy) S.p.A.

  公开号：US06350873B2

  公开（公告）日：2002-02-26

  The present invention relates to a process for preparing 5′-acetylstavudine, an intermediate which is useful in the preparation of 2′,3′-didehydro-3′-deoxythymidine, an active principle with antiviral action which is commonly known as stavudine (D4T).

  这项发明涉及一种制备5'-乙酰司他夫定的过程，该中间体在制备2',3'-二去氢-3'-脱氧胸苷（一种常称为司他夫定（D4T）的具有抗病毒作用的活性成分）中有用。