(-)-(3R,4R)-trans-tetrahydropyran-3,4-diol | 79026-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (-)-(3R,4R)-trans-tetrahydropyran-3,4-diol
• 英文别名: rac-(3R,4R)-oxane-3,4-diol,trans；(3S,4S)-oxane-3,4-diol
• CAS: 79026-40-7
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: PIWMSRFXAJSGLP-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(3R,4R)-trans-tetrahydropyran-3,4-diol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 生成 (2S)-2-amino-3-(hydroxy{(3S,4S)-3-[3-(2-undecyloxy-phenyl)propionyloxy]tetrahydropyran-4-yloxy}phosphoryloxy)propionic acid acetic acid
  参考文献：
  名称：

  Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors

  摘要：

  Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of L-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure- activity relationship studies of more than 100 "glycol surrogate" derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1- and 2-acyl lysophospholipids.

  DOI：

  10.1021/acs.jmedchem.0c01126
• 作为产物：
  描述：

  L-xylopyranose 在 palladium on activated charcoal 吡啶 、 甲醇 、 氢溴酸 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (-)-(3R,4R)-trans-tetrahydropyran-3,4-diol
  参考文献：
  名称：

  通过使用碳水化合物支架来鉴定特定构象：发现亚型选择性LPA受体激动剂和拮抗剂。

  摘要：

  DOI：

  10.1002/anie.200454065

文献信息

• Unusual steric course of the epoxide hydrolase-catalyzed hydrolysis of (.+-.)-3,4-epoxytetrahydropyran. A case of complete stereoconvergence
  作者：Giuseppe Bellucci、Giancarlo Berti、Giorgio Catelani、Ettore Mastrorilli

  DOI：10.1021/jo00338a016

  日期：1981.12
• Identifying Specific Conformations by Using a Carbohydrate Scaffold: Discovery of Subtype-Selective LPA-Receptor Agonists and an Antagonist
  作者：Yoko Tamaruya、Masato Suzuki、Goshu Kamura、Motomu Kanai、Kotaro Hama、Kumiko Shimizu、Junken Aoki、Hiroyuki Arai、Masakatsu Shibasaki

  DOI：10.1002/anie.200454065

  日期：2004.5.17
• Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors
  作者：Sho Nakamura、Misa Sayama、Akiharu Uwamizu、Sejin Jung、Masaya Ikubo、Yuko Otani、Kuniyuki Kano、Jumpei Omi、Asuka Inoue、Junken Aoki、Tomohiko Ohwada

  DOI：10.1021/acs.jmedchem.0c01126

  日期：2020.9.10

  Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of L-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure- activity relationship studies of more than 100 "glycol surrogate" derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1- and 2-acyl lysophospholipids.