isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate | 868785-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate
• 英文别名: danshensu isopropyl ester；isopropyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate；IDHP；propan-2-yl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate
• CAS: 868785-50-6
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: ZYFWDUKUSGLMGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate 在 NOVASEP-SFC 3050, CHIRALPAK AD-H 作用下， 以 甲醇 、 水 为溶剂， 以87%的产率得到(S)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  Improved Process for Pilot-Scale Synthesis of Danshensu ((±)-DSS) and Its Enantiomer Derivatives

  摘要：

  A pilot-scale process has been developed for green and scalable synthesis of (+/-)-beta-(3,4-dihydroxyphenyl) lactic acid ((+/-)-DSS) and their two important derivatives, namely, (+/-)-IDHP [(+/-)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (+/-)-DBZ [(+/-)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (+/-)-DBZ and 49.2% for (+/-)-IDHP compared to the initial process with a yield of 12% for (+/-)-DBZ and 18% for (+/-)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(-)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(-)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).

  DOI：

  10.1021/op4002593
• 作为产物：
  描述：

  (Z)-3-(3,4-二羟基苯基)-2-羟基丙烯酸 在 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 正己烷 为溶剂， 60.0~70.0 ℃ 、1.0 MPa 条件下， 反应 33.0h， 生成 isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  Improved Process for Pilot-Scale Synthesis of Danshensu ((±)-DSS) and Its Enantiomer Derivatives

  摘要：

  A pilot-scale process has been developed for green and scalable synthesis of (+/-)-beta-(3,4-dihydroxyphenyl) lactic acid ((+/-)-DSS) and their two important derivatives, namely, (+/-)-IDHP [(+/-)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (+/-)-DBZ [(+/-)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (+/-)-DBZ and 49.2% for (+/-)-IDHP compared to the initial process with a yield of 12% for (+/-)-DBZ and 18% for (+/-)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(-)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(-)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).

  DOI：

  10.1021/op4002593

文献信息

• 一种混旋丹参素异丙酯的合成方法
  申请人：西北大学

  公开号：CN103980120B

  公开（公告）日：2018-02-16

  本发明涉及一种混旋丹参素异丙酯的合成方法，方法包括以原儿茶醛为初始原料，经苄基保护酚羟基，Darzens环氧化，再经再经钯类催化剂/氢气或雷尼镍/氢气催化还原，得到混旋丹参素异丙酯。本发明的方法合成的产品纯度可达98％，产率可达55％。且本发明的合成方法，原料简单易得，路线短，产率高，适合大规模工业化生产。
• GLYCAN THERAPEUTICS AND RELATED METHODS THEREOF
  申请人：Kaleido Biosciences, Inc.

  公开号：EP3071235A1

  公开（公告）日：2016-09-28
• GLYCAN COMPOSITIONS AND USES THEREOF
  申请人：Kaleido Biosciences, Inc.

  公开号：EP3334437A1

  公开（公告）日：2018-06-20
• [EN] GLYCAN THERAPEUTICS AND RELATED METHODS THEREOF<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES DE GYLCANE ET PROCÉDÉS ASSOCIÉS
  申请人：KALEIDO BIOSCIENCES INC

  公开号：WO2016122889A1

  公开（公告）日：2016-08-04

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.
• [EN] GLYCAN COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSITIONS DE GLYCANE ET LEURS UTILISATIONS
  申请人：KALEIDO BIOSCIENCES INC

  公开号：WO2017035412A1

  公开（公告）日：2017-03-02

  Compositions comprising glycan preparations suitable for local administration to non-gut sites containing mucosal tissue, e.g., oral cavity, nasal cavity and vagina are provided. Further provided are methods of using said glycan preparations.