benzyl (S)-2,3-dihydroxypropionate | 104640-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (S)-2,3-dihydroxypropionate
• 英文别名: benzyl (S)-glycerate；benzyl (2S)-2,3-dihydroxypropanoate
• CAS: 104640-62-2
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: RDONDBREQKWFBL-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (S)-2,3-dihydroxypropionate 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 TEA 、 硫酸 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 benzyl (R)-3-tert-butyloxy-2-phthalimidooxypropanoate
  参考文献：
  名称：

  由L-氨基酸或L-羟基酸合成光学活性的邻苯二甲酰基D-氨基氧基酸，作为制备氨基氧基肽的基础。

  摘要：

  DOI：

  10.1021/jo0006573
• 作为产物：
  描述：

  丙烯酸苄酯 在 potassium dioxotetrahydroxoosmate(VI) 、 水 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 叔丁醇 为溶剂， 生成 (2R)-benzyl 2,3-dihydroxypropanoate 、 benzyl (S)-2,3-dihydroxypropionate
  参考文献：
  名称：

  The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement

  摘要：

  Two key improvements in the osmium-catalyzed asymmetric dihydroxylation have l

  DOI：

  10.1021/jo00036a003

文献信息

• THIAZOLE DERIVATIVE
  申请人：Astellas Pharma Inc.

  公开号：EP1921074A1

  公开（公告）日：2008-05-14

  [Problem] To provide a compound which is useful as a GK activator. [Means for Resolution] As a result of an extensive study on thiazole derivatives, the present inventors have found that a compound having an oxamoyl group, a glycol group or the like on a thiazole ring and a compound having an acetamide group substituted by a bicyclic heteroaryl group such as a quinolyl have a good GK activation effect, and thereby have accomplished the present invention. Since the compounds of the present invention have a good GK activation effect, these are useful as therapeutic agents for diabetes, particularly type II diabetes.

  [问题] 提供一种作为GK激活剂有用的化合物。[解决方法] 通过对噻唑衍生物进行广泛研究，本发明人发现，在噻唑环上具有氧羰基、甘醇基或类似基团的化合物，以及在乙酰胺基团上被双环杂环芳基团（如喹啉基）取代的化合物具有良好的GK激活效果，从而完成了本发明。由于本发明的化合物具有良好的GK激活效果，因此它们可用作糖尿病的治疗药物，特别是II型糖尿病。
• Becker, Heinrich; Sharpless, K. Barry, Angewandte Chemie, 1996, vol. 108, # 4, p. 447 - 449
  作者：Becker, Heinrich、Sharpless, K. Barry

  DOI：——

  日期：——
• Synthesis and CB1 receptor activities of novel arachidonyl alcohol derivatives
  作者：Teija Parkkari、Juha R. Savinainen、Anu L. Rauhala、Tiina L. Tolonen、Tapio Nevalainen、Jarmo T. Laitinen、Jukka Gynther、Tomi Järvinen

  DOI：10.1016/j.bmcl.2004.03.093

  日期：2004.6

  Novel derivatives of arachidonyl alcohol were synthesized and evaluated for their CBI receptor activity by [S-35]GTP(gamma)S assay using rat cerebellar membranes. (C) 2004 Elsevier Ltd. All rights reserved.
• The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement
  作者：K. Barry Sharpless、Willi Amberg、Youssef L. Bennani、Gerard A. Crispino、Jens Hartung、Kyu Sung Jeong、Hoi Lun Kwong、Kouhei Morikawa、Zhi Min Wang

  DOI：10.1021/jo00036a003

  日期：1992.5

  Two key improvements in the osmium-catalyzed asymmetric dihydroxylation have l
• Chemical and Electrochemical Asymmetric Dihydroxylation of Olefins in I₂−K₂CO₃−K₂OsO₂(OH)₄ and I₂−K₃PO₄/K₂HPO₄−K₂OsO₂(OH)₄ Systems with Sharpless' Ligand
  作者：Sigeru Torii、Ping Liu、Narayanaswamy Bhuvaneswari、Christian Amatore、Anny Jutand

  DOI：10.1021/jo952137r

  日期：1996.1.1

  Iodine-assisted chemical and electrochemical asymmetric dihydroxylation of various olefins in I-2-K2CO3-K2OsO2(OH)(4) and I-2-K3PO4/K2HPO4-K2OsO2(OH)(4) systems with Sharpless' ligand provided the optically active glycols in excellent isolated yields and high enantiomeric excesses. Iodine (I-2) was used stoichiometrically for the chemical dihydroxylation, and good results were obtained with nonconjugated olefins in contrast to the case of potassium ferricyanide as a co-oxidant. The potentiality of I-2 as a co-oxidant under stoichiometric conditions has been proven to be effective as an oxidizing mediator in electrolysis systems. Iodine-assisted asymmetric electro-dihydroxylation of olefins in either a t-BuOH/H2O(1/1)-K2CO3/(DHQD)(2)PHAL-(Pt) or t-BuOH/H2O(1/1)-K3PO4/ K2HPO4/(DHQD)(2)PHAL-(Pt) system in the presence of potassium osmate in an undivided cell was investigated in detail. Irrespective of the substitution pattern, all the olefins afforded the diols in high yields and excellent enantiomeric excesses. A plausible mechanism is discussed on the basis of cyclic voltammograms as well as experimental observations.