(2R)-benzyl 2,3-dihydroxypropanoate | 55032-35-4

• 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: (2R)-benzyl 2,3-dihydroxypropanoate
• 英文别名: benzyl (R)-2,3-dihydroxypropionate；(R)-2,3-dihydroxy-propionic acid benzyl ester；D-Glycerinsaeure-benzylester；(R)-benzyl 2,3-dihydroxypropanoate；benzyl (2R)-2,3-dihydroxypropanoate
• CAS: 55032-35-4
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: RDONDBREQKWFBL-SECBINFHSA-N

物化性质

• 沸点：
  367.8±12.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

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：

  (2R)-benzyl 2,3-dihydroxypropanoate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Solution-Phase and Solid-Phase Syntheses of Enzyme Inhibitor RK-682 and Antibiotic Agglomerins

  摘要：

  The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph-3-PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.

  DOI：

  10.1021/jo050797i
• 作为产物：
  描述：

  (4R)-4-benzyloxycarbonyl-2,2-dimethyl-1,3-dioxolane 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (2R)-benzyl 2,3-dihydroxypropanoate
  参考文献：
  名称：

  Solution-Phase and Solid-Phase Syntheses of Enzyme Inhibitor RK-682 and Antibiotic Agglomerins

  摘要：

  The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph-3-PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.

  DOI：

  10.1021/jo050797i

文献信息

• Becker, Heinrich; Sharpless, K. Barry, Angewandte Chemie, 1996, vol. 108, # 4, p. 447 - 449
  作者：Becker, Heinrich、Sharpless, K. Barry

  DOI：——

  日期：——
• 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.
• 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
• Wulff,G. et al., Chemische Berichte, 1974, vol. 107, p. 3364 - 3376
  作者：Wulff,G. et al.

  DOI：——

  日期：——