diethyl 2-(tert-butyldimethylsilyloxymethyl)-2-(methylthiomethyloxymethyl)malonate | 1161393-27-6

• 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: diethyl 2-(tert-butyldimethylsilyloxymethyl)-2-(methylthiomethyloxymethyl)malonate
• 英文别名: diethyl 2-(tert-butyldimethylsilyloxymethyl)-2-methylthiomethoxymethylmalonate；diethyl 2-(tert-butyldimethylsilyloxymethyl)-2-methylthiomethylmalonate；Diethyl 2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(methylsulfanylmethoxymethyl)propanedioate
• CAS: 1161393-27-6
• 化学式: C₁₇H₃₄O₆SSi
• 分子量: 394.605
• InChiKey: HHYBURUIIUVTQD-UHFFFAOYSA-N

物化性质

• 沸点：
  425.3±45.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 2-(tert-butyldimethylsilyloxymethyl)-2-(methylthiomethyloxymethyl)malonate 在 磺酰氯 、 二苯并-18-冠醚-6 、 potassium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.67h， 以71%的产率得到diethyl 2-acetyloxymethyloxymethyl-2-(tert-butyldimethylsilyloxymethyl)malonate
  参考文献：
  名称：

  2-5A ANALOGS AND THEIR METHODS OF USE

  摘要：

  本文披露了激活RNaseL的化合物，合成激活RNaseL的化合物的方法，以及利用激活RNaseL的化合物用于治疗和/或改善疾病或病况，如病毒感染、癌症和/或寄生虫病。

  公开号：

  US20090181921A1
• 作为产物：
  描述：

  diethyl 2-(tert-butyldimethylsilyloxymethyl)-2-hydroxymethylmalonate 、 二甲基亚砜 在 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 以91%的产率得到diethyl 2-(tert-butyldimethylsilyloxymethyl)-2-(methylthiomethyloxymethyl)malonate
  参考文献：
  名称：

  [EN] SUBSTITUTED NUCLEOSIDE AND NUCLEOTIDE ANALOGS
  [FR] NUCLEOSIDE SUBSTITUE ET ANALOGUES NUCLEOTIDIQUES

  摘要：

  本文披露了具有保护磷酸酯基团的核苷酸类似物，以及合成具有保护磷酸酯基团的核苷酸类似物的方法，以及利用具有保护磷酸酯基团的核苷酸类似物治疗病毒感染、癌症和/或寄生虫病等疾病和/或症状的方法。

  公开号：

  WO2010108140A1

文献信息

• PROTECTED NUCLEOTIDE ANALOGS
  申请人：Beigelman Leonid

  公开号：US20090176732A1

  公开（公告）日：2009-07-09

  Disclosed herein are nucleotide analogs with one or more protecting groups, methods of synthesizing nucleotide analogs with one or more protecting groups and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the nucleotide analogs with one or more protecting groups.

  本文披露了具有一个或多个保护基团的核苷酸类似物，合成具有一个或多个保护基团的核苷酸类似物的方法，以及利用具有一个或多个保护基团的核苷酸类似物治疗疾病和/或病况，如病毒感染、癌症和/或寄生虫病的方法。
• Biodegradable Protections for Nucleoside 5′-Monophosphates: Comparative Study on the Removal of <i>O</i>-Acetyl and <i>O</i>-Acetyloxymethyl Protected 3-Hydroxy-2,2-bis(ethoxycarbonyl)propyl Groups
  作者：Mikko Ora、Sharmin Taherpour、Risto Linna、Anna Leisvuori、Emilia Hietamäki、Päivi Poijärvi-Virta、Leonid Beigelman、Harri Lönnberg

  DOI：10.1021/jo9005987

  日期：2009.7.17

  The applicability of 3-acetyloxy-2,2-bis(ethoxycarbonyl)propyl and 3-acetyloxymethoxy-2,2-bis(ethoxycarbonyl)propyl groups as biodegradable phosphate protecting groups for nucleoside 5'-monophosphates has been studied in a HEPES buffer at pH 7.5. Enzymatic deacetylation with porcine carboxyesterase triggers the removal of the resulting 3 -hydroxy-2,2-bis(ethoxycarbonyl)propyl and 3-hydroxymethoxy-2,2-bis(ethoxycarbonyl)propyl groups by retro-aldol condensation and consecutive half acetal hydrolysis and retro-aldol condensation, respectively. The kinetics of these multistep deprotection reactions have been followed by HPLC, using appropriately protected thymidine 5'-monophosphates as model compounds. The enzymatic deacetylation of the 3-acetyloxymethoxy-2,2-bis(ethoxycarbonyl)propyl 5'-triester (2) is 25-fold faster than the deacetylation of its 3-acetyloxy-2,2-bis(ethoxycarbonyl)propyl-protected counterpart 1, and the difference in the deacetylation rates of the resulting diesters, 12b and 12a, is even greater. With 2, conversion to thymidine 5'-monophosphate (5'-TMP) is quantitative, while conversion of 1 to 5'-TMP is accompanied by formation of thymidine. Consistent with the preceding observations, quantitative release of 5'-TMP from 2 has been shown to take place in a whole cell extract of human prostate cancer cells.
• [EN] SUBSTITUTED NUCLEOSIDE AND NUCLEOTIDE ANALOGS<br/>[FR] NUCLEOSIDE SUBSTITUE ET ANALOGUES NUCLEOTIDIQUES
  申请人：ALIOS BIOPHARMA INC

  公开号：WO2010108140A1

  公开（公告）日：2010-09-23

  Disclosed herein are nucleotide analogs with protected phosphates, methods of synthesizing nucleotide analogs with protected phosphates and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the nucleotide analogs with protected phosphates.

  本文披露了具有保护磷酸酯基团的核苷酸类似物，以及合成具有保护磷酸酯基团的核苷酸类似物的方法，以及利用具有保护磷酸酯基团的核苷酸类似物治疗病毒感染、癌症和/或寄生虫病等疾病和/或症状的方法。
• 2-5A ANALOGS AND THEIR METHODS OF USE
  申请人：Blatt Lawrence

  公开号：US20090181921A1

  公开（公告）日：2009-07-16

  Disclosed herein are compounds that activate RNaseL, methods of synthesizing compounds that activate RNaseL and the use of compounds that activate RNaseL for treating and/or ameliorating a disease or a condition, such as a viral infection, cancer and/or parasitic disease.

  本文披露了激活RNaseL的化合物，合成激活RNaseL的化合物的方法，以及利用激活RNaseL的化合物用于治疗和/或改善疾病或病况，如病毒感染、癌症和/或寄生虫病。