2-methyl-2-propionyloxy-propionyl chloride | 58570-07-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methyl-2-propionyloxy-propionyl chloride
• 英文别名: (1-Chloro-2-methyl-1-oxopropan-2-yl) propanoate
• CAS: 58570-07-3
• 化学式: C₇H₁₁ClO₃
• 分子量: 178.616
• InChiKey: SJRKENZSJMNFMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2-propionyloxy-propionyl chloride 、 胞苷 生成 (3aS)-2t-hydroxymethyl-3c-propionyloxy-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine
  参考文献：
  名称：

  2-酰氧基异丁酰卤化物与核苷的反应。6.2,2'-脱水-1-（β-D-阿拉伯呋喃糖基）胞嘧啶盐酸盐的一些3'-酰基衍生物的合成和生物学评价。

  摘要：

  胞苷与22种不同的2-O-酰氧基异丁酰氯的反应导致分离出相应的2,2'-脱水-1-（3'-O-酰基-β-d-阿拉伯呋喃糖基）胞嘧啶盐酸盐9。这些化合物，所有这些都显示出对组织培养物中的HeLa细胞具有细胞毒性，已经检查了其抗病毒和抗白血病活性。在组织培养中，对具有DNA带有8--12个碳原子的酰基的化合物，DNA病毒（牛痘和疱疹）的活性最大。小鼠对L1210白血病的活性随酰基长度的变化而显着变化，长链（C16-C22）酯具有很高的活性。胞苷与O-乙酰基水杨酰氯之间的反应为合成3'-O-Ac环C盐酸盐提供了另一种途径。

  DOI：

  10.1021/jm00227a016

文献信息

• Method for the synthesis of 2',3'-dideoxy-2',3'-didehydronucleosides
  申请人：——

  公开号：US20020198224A1

  公开（公告）日：2002-12-26

  The present invention is an efficient synthetic route to 2′,3′-dideoxy-2′,3 ′-didehydro-nucleosides from available precursors with the option of introducing functionality as needed, such as, the 2′,3′-dideoxy and 2′- or 3′-deoxyribo-nucleoside analogs as well as additional derivatives obtained by subsequent functional group manipulations. Briefly, the present invention discloses a method for the preparation of &bgr;-D and &bgr;-L-2′,3′-dideoxy-2′,3′-didehydro-nucleosides starting from appropriately substituted ribonucleosides in two, optionally three steps: Step (1) a haloacylation, such as haloacetylation, and in particular, bromoacetylation; Step (2) a reductive elimination; and optionally, Step (3) a deprotection. The haloacylation of step (1) can form the 2′-acyl-3′-halonucleoside, the 3′-acyl-2′-halonucleoside, or a mixture thereof.

  本发明提供了一种高效的合成路线，可以从可用的前体物开始合成2'，3'-二脱氧-2'，3'-二脱氢核苷，同时可以根据需要引入功能，例如2'，3'-二脱氧和2'-或3'-脱氧核糖核苷类似物以及通过后续的官能团操作获得的额外衍生物。简而言之，本发明揭示了一种制备β-D和β-L-2'，3'-二脱氧-2'，3'-二脱氢核苷的方法，从适当取代的核糖核苷开始，在两个可选的步骤中进行：步骤（1）卤代酰化，例如卤代乙酰化，特别是溴代乙酰化；步骤（2）还原消除；可选地，步骤（3）去保护基。步骤（1）的卤代酰化可以形成2'-酰基-3'-卤代核苷，3'-酰基-2'-卤代核苷或它们的混合物。
• METHOD FOR THE SYNTHESIS OF 2',3'-DIDEOXY-2',3'-DIDEHYDRONUCLEOSIDES
  申请人：Pharmasset Limited

  公开号：EP1363927A2

  公开（公告）日：2003-11-26
• US6927291B2
  申请人：——

  公开号：US6927291B2

  公开（公告）日：2005-08-09
• [EN] METHOD FOR THE SYNTHESIS OF 2',3'-DIDEOXY-2',3'-DIDEHYDRONUCLEOSIDES<br/>[FR] PROCEDE DE SYNTHESE DE 2',3'-DIDEOXY-2',3'-DIDEHYDRONUCLEOSIDES
  申请人：PHARMASSET LTD

  公开号：WO2002070533A2

  公开（公告）日：2002-09-12

  The present invention is an efficient synthetic route to 2',3'-dideoxy-2',3'-didehydro-nucleosides from available precursors with the option of introducing functionality as needed, such as, the 2',3'-dideoxy and 2'- or 3'-deoxyribo-nucleoside analogs as well as additional derivatives obtained by subsequent functional group manipulations. Briefly, the present invention discloses a method for the preparation of β-D and β-L-2',3'-dideoxy-2',3'-didehydro-nucleosides starting from appropriately substituted ribonucleosides in two, optionally three steps: Step (1) a haloacylation, such as haloacetylation, and in particular, bromoacetylation; Step (2) a reductive elimination; and optionally, Step (3) a deprotection. The haloacylation of step (1) can form the 2'-acyl-3'-halonucleoside, the 3'-acyl-2'-halonucleoside, or a mixture thereof.