(2S)-(-)-O-(tetrahydropyran-2-yl)-3-phenyllactic acid | 90476-29-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S)-(-)-O-(tetrahydropyran-2-yl)-3-phenyllactic acid
• 英文别名: (2S)-2-(oxan-2-yloxy)-3-phenylpropanoic acid
• CAS: 90476-29-2
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: FJCBXKURTHGDPO-UEWDXFNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-(-)-O-(tetrahydropyran-2-yl)-3-phenyllactic acid 在 盐酸 作用下， 反应 1.25h， 生成 (S)-3-Phenyllactoyl-(R)-prolyl-(S)-alanyl-aminoisobutyrolacton
  参考文献：
  名称：

  合成酶cyclischen Depsipeptides mittels Amidcyclisierung

  摘要：

  通过酰胺环合反应合成环二肽

  DOI：

  10.1002/hlca.19840670221
• 作为产物：
  描述：

  L-(-)-3-苯基乳酸 在 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 23.08h， 生成 (2S)-(-)-O-(tetrahydropyran-2-yl)-3-phenyllactic acid
  参考文献：
  名称：

  Characterization of an abeo-Taxane:  Brevifoliol and Derivatives

  摘要：

  Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the C-13 NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.

  DOI：

  10.1021/np0304565

文献信息

• Solid phase synthesis of N-aminodipeptides in high optical purity
  作者：Anne-Sophie Felten、Régis Vanderesse、Nicolas Brosse、Claude Didierjean、Brigitte Jamart-Grégoire

  DOI：10.1016/j.tetlet.2007.10.152

  日期：2008.1

  N-Aminodipeptide derivatives can be easily prepared with high optical purity on solid phase via a Mitsunobu protocol between a solid supported α-hydroxyacid and a free phthaloylated α-Z-N-aminohydrazide.

  通过固载的α-羟基酸和游离的邻苯二甲酰化的α- Z - N-氨基酰肼之间的Mitsunobu方案，可以容易地在固相上以高光学纯度制备N-氨基二肽衍生物。
• FORMULATIONS COMPRISING CYCLIC COMPOUNDS
  申请人：Botti Paolo

  公开号：US20100137188A1

  公开（公告）日：2010-06-03

  This invention relates to the use of a cyclic compound of formula (I) wherein A, B independently in each occurrence is alkane-i,j-diyl having k carbon atoms, i and independently j being less than or equal k and k being selected from 1 to 10, wherein said alkane-i,j-diyl (i) may comprise one or more double bonds; (ii) is optionally substituted; and/or (iii) comprises a cycle, wherein the total number of cycles being cyclic sugars in said compound is selected from 0 to 4 and is less than p·n+m); X,Y independently in each occurrence is a biocompatible functional group comprising at least one oxygen atom or two sulphur atoms; n, m independently of each other are selected from 0 to 20; p is selected from 1 to 10; n+m is equal or greater than 1; and p·(n+m) is selected from 3 to 30; wherein said compound is capable of forming a complex with a protonated primary and/or protonated secondary amino group and/or a protonated guanidinium group for the manufacture of a pharmaceutical or diagnostic composition further comprising a pharmaceutically or diagnostically active agent, said active agent comprising one or more protonated primary and/or protonated secondary amino groups and/or a protonated guanidinium groups, wherein (a) transmembrane and/or transmucosal delivery; (b) solubility in non-aqueous solvents; and/or (c) stability of said active agent are improved.
• US8513188B2
  申请人：——

  公开号：US8513188B2

  公开（公告）日：2013-08-20
• Characterization of an <i>a</i><i>beo</i>-Taxane:  Brevifoliol and Derivatives
  作者：Steve Tremblay、Chantal Soucy、Neil Towers、Philip J. Gunning、Livain Breau

  DOI：10.1021/np0304565

  日期：2004.5.1

  Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the C-13 NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.
• Synthese eines cyclischen Depsipeptides mittels Amidcyclisierung
  作者：Daniel Obrecht、Heinz Heimgartner

  DOI：10.1002/hlca.19840670221

  日期：1984.3.14

  Synthesis of a Cyclic Depsipeptide via an Amide Cyclization

  通过酰胺环合反应合成环二肽