[(1S)-1-[(甲氧基甲基氨基)羰基]丁基]氨基甲酸苄酯 | 207728-22-1

• 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
• 中文名称: [(1S)-1-[(甲氧基甲基氨基)羰基]丁基]氨基甲酸苄酯
• 英文名称: (S)-N-benzyloxycarbonylamino-N-methoxy-N-methylnorvalinamide
• 英文别名: [(1S)-1-[(Methoxymethylamino)carbonyl]butyl]carbamic Acid Benzyl Ester；benzyl N-[(2S)-1-[methoxy(methyl)amino]-1-oxopentan-2-yl]carbamate
• CAS: 207728-22-1
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: ZEIXIJCWVDGXTR-ZDUSSCGKSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S)-1-[(甲氧基甲基氨基)羰基]丁基]氨基甲酸苄酯 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 3.5h， 生成 4-aminoundecan-5-ol
  参考文献：
  名称：

  Auxiliary Agents for the Peroral Administration of Peptide and Protein Drugs:  Synthesis and Evaluation of Novel Pepstatin Analogues

  摘要：

  The peroral administration of(poly)peptide drugs requires the development of delivery systems, which provide a protective effect toward a gastrointestinal enzymatic attack. A promising strategy for such systems represents polymer-enzyme inhibitor conjugates in which the embedded therapeutic agent is protected. However, the practical use of polymer-inhibitor conjugates has so far been limited by high production costs of these auxiliary agents. To solve this problem for delivery systems shielding from pepsinic degradation, structurally simplified analogues of the pepsin inhibitor pepstatin A have been synthesized. The synthesis of tripeptide analogues, described by McConnell et al., led us to pursue further modifications varying the C-terminus. Our target to attach a spacer moisty-enabling the free access of pepsin to the inhibitor-should be combined with an attractive synthetic approach providing low production costs in large-scale preparation. Structure modifications comprised either the side chain of the third amino acid which served as starting compound designing the C-terminus (L-leucine, L-isoleucine, L-norvaline) as the length of the spacer link, simulated by a linear alkyl group (n-butyl, n-hexyl, and n-octyl). The inhibitory activities which have been evaluated by an enzyme assay were significantly dependent on the nature of the side chain, whereas the length of the spacer had no influence on the inhibitory effect. Analogues bearing the isobutyl or n-propyl moiety as side chain displayed a strong inhibitory effect which was comparable to that pepstatin A. These congeners represent promising auxiliary agents for the peroral administration of(poly)peptide drugs.

  DOI：

  10.1021/jm980015w
• 作为产物：
  描述：

  L-正缬氨酸 在 N-甲基吗啉 、 sodium hydroxide 、 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride 、 sodium carbonate 、 1-羟基苯并三唑一水物 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 [(1S)-1-[(甲氧基甲基氨基)羰基]丁基]氨基甲酸苄酯
  参考文献：
  名称：

  对映选择性合成和绝对构型的（-）-1-（苯并呋喃-2-基）-2-丙基氨基戊烷（（-）-BPAP），一种高效的选择性儿茶酚胺能增强剂。

  摘要：

  描述了（-）-1-（苯并呋喃-2-基）-2-丙基氨基戊烷（（-）-BPAP）的对映选择性合成和绝对构型，这是一种高效且选择性的儿茶酚胺能活性增强剂（CAE）物质。合成方法包括苯并呋喃与（R）-N-甲苯磺酰基-2-丙基叠氮嗪或（R）-N-甲氧基-N-甲基降甲酰胺的偶联反应，然后对所得偶联产物进行适当的修饰。结果，（-）-BPAP证明具有R构型，其最终通过X射线晶体学分析得到证实。

  DOI：

  10.1016/s0968-0896(00)00341-2

文献信息

• Processes and intermediates
  申请人：Tanoury J. Gerald

  公开号：US20070087973A1

  公开（公告）日：2007-04-19

  The invention relates to compounds and processes useful for the preparation of protease inhibitors, particularly serine protease inhibitors. The protease inhibitors are useful for treatment of HCV infections.

  这项发明涉及到化合物和工艺，用于制备蛋白酶抑制剂，特别是丝氨酸蛋白酶抑制剂。这些蛋白酶抑制剂对治疗HCV感染很有用。
• SYNTHESIS OF AN INTERMEDIATE OF AN ANTIVIRAL COMPOUND
  申请人：ALLEGRINI Pietro

  公开号：US20140148574A1

  公开（公告）日：2014-05-29

  Process for the preparation of a cyclopropylamide compound which is useful as a structural unit in a process for the preparation of a viral protease inhibitor.

  用作病毒蛋白酶抑制剂制备过程中的结构单元的环丙胺化合物的制备过程。
• Synthesis of an intermediate of an antiviral compound
  申请人：Dipharma Francis S.r.l.

  公开号：EP2738164A1

  公开（公告）日：2014-06-04

  Process for the preparation of a cyclopropylamide compound (II) which is useful as a structural unit in a process for the preparation of a viral protease inhibitor.

  用于制备一种环丙基酰胺化合物（II）的过程，该化合物在制备病毒蛋白酶抑制剂的过程中作为结构单元有用。
• PROCESSES AND INTERMEDIATES
  申请人：Tanoury Gerald J.

  公开号：US20100063252A1

  公开（公告）日：2010-03-11

  The invention relates to compounds and processes useful for the preparation of protease inhibitors, particularly serine protease inhibitors. The protease inhibitors are useful for treatment of HCV infections.

  该发明涉及化合物和工艺，用于制备蛋白酶抑制剂，特别是丝氨酸蛋白酶抑制剂。这些蛋白酶抑制剂对治疗HCV感染很有用。
• Processes and intermediates for preparing steric compounds
  申请人：Tanoury J. Gerald

  公开号：US20070244334A1

  公开（公告）日：2007-10-18

  This invention relates to processes and intermediates for the preparation of an alpha-amino beta-hydroxy acid of Formula 1 wherein the variables R 1 , R′ 1 and R 2 are defined herein and the compound of Formula 1 has an enantiomeric excess (ee) of 55% or greater.

  本发明涉及制备式1的α-氨基β-羟基酸的过程和中间体，其中变量R1、R′1和R2在此定义，式1的化合物的对映体过量（ee）为55％或更高。