2,3-Dideoxy-4,5-O-(1-methylethylidene)-3-(nitromethyl)-L-threo-pentonic Acid Ethyl Ester | 501921-23-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3-Dideoxy-4,5-O-(1-methylethylidene)-3-(nitromethyl)-L-threo-pentonic Acid Ethyl Ester
• 英文别名: ethyl (3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-nitrobutanoate
• CAS: 501921-23-9
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: AUDIVQVJJMELHM-BDAKNGLRSA-N

物化性质

• 沸点：
  354.1±27.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-Dideoxy-4,5-O-(1-methylethylidene)-3-(nitromethyl)-L-threo-pentonic Acid Ethyl Ester 在 甲醇 、 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 (3R,3AS,6AR)-六氢呋喃并[2,3-B]呋喃-3-醇
  参考文献：
  名称：

  Stereoselective and Efficient Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol

  摘要：

  [GRAPHICS]Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.

  DOI：

  10.1021/ol052554i
• 作为产物：
  描述：

  硝基甲烷 、 ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 2,3-Dideoxy-4,5-O-(1-methylethylidene)-3-(nitromethyl)-L-threo-pentonic Acid Ethyl Ester
  参考文献：
  名称：

  Stereoselective and Efficient Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol

  摘要：

  [GRAPHICS]Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.

  DOI：

  10.1021/ol052554i

文献信息

• De Novo Synthesis of Conjugates
  申请人：Riggs-Sauthier Jennifer

  公开号：US20100184989A1

  公开（公告）日：2010-07-22

  The invention provides methods for the preparation of small molecule drugs that are chemically modified by covalent attachment of a water-soluble oligomer obtained from a water-soluble oligomer composition. Such drugs are produced through modification of a synthetic pathway to attach the oligomer to an intermediate compound followed by completion of the synthetic path.

  本发明提供了一种制备化学修饰的小分子药物的方法，其中化学修饰是通过共价连接来自水溶性寡聚物组合物的水溶性寡聚物进行的。这种药物是通过修改合成途径将寡聚物连接到中间化合物，然后完成合成途径而生产的。
• Oligomer-Protease Inhibitor Conjugates
  申请人：Riggs-Sauthier Jennifer

  公开号：US20110269677A1

  公开（公告）日：2011-11-03

  The invention provides protease inhibitors that are chemically modified by covalent attachment of a water-soluble oligomer. A conjugate of the invention, when administered by any of a number of administration routes, exhibits characteristics that are different from the protease inhibitors not attached to the water-soluble oligomer.

  该发明提供了通过共价连接水溶性寡聚体进行化学修饰的蛋白酶抑制剂。该发明的结合物在通过任何一种给药途径进行给药时，表现出与未连接水溶性寡聚体的蛋白酶抑制剂不同的特性。
• OLIGOMER-PROTEASE INHIBITOR CONJUGATES
  申请人：NEKTAR THERAPEUTICS

  公开号：US20140045770A1

  公开（公告）日：2014-02-13

  The invention provides small molecule drugs that are chemically modified by covalent attachment of a water-soluble oligomer. A conjugate of the invention, when administered by any of a number of administration routes, exhibits characteristics that are different from the small molecule drug not attached to the water-soluble oligomer.

  本发明提供了通过共价结合水溶性寡聚物进行化学修饰的小分子药物。本发明的结合物在通过任何一种给药途径给予时，表现出与未连接水溶性寡聚物的小分子药物不同的特性。
• Process for the preparation of [(1S,2R)-3-[[(4-aminophenyl)sulfonyl] (2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid (3R,3AS,6AR)hexahydro furo [2,3-B]furan-3-YL ester and its amorphous form
  申请人：MSN LABORATORIES PRIVATE LIMITED

  公开号：US10633390B2

  公开（公告）日：2020-04-28

  The present invention relates to an improved process for the preparation of [(1S,2R)-3-[[(4-aminophenyl)sulfonyl] (2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl ester compound of formula-1 represented by the following structural formula:

  本发明涉及一种制备[(1S,2R)-3-[[(4-氨基苯基)磺酰基](2-甲基丙基)氨基]-2-羟基-1-(苯基甲基)丙基]-氨基甲酸 (3R,3aS,6aR)六氢呋喃并[2,3-b]呋喃-3-基]式-1化合物的改进工艺，其结构式如下：
• Oligomer-protease inhibitor conjugates
  申请人：Nektar Therapeutics

  公开号：EP2522367B1

  公开（公告）日：2016-01-20