(3S,4R)-tetrahydropyran-3,4-diol | 115015-46-8

• 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: (3S,4R)-tetrahydropyran-3,4-diol
• 英文别名: L-erythro-1,5-anhydro-2-deoxy-pentitol；L-erythro-1,5-Anhydro-2-desoxy-pentit；(3S,4R)-oxane-3,4-diol
• CAS: 115015-46-8
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: PIWMSRFXAJSGLP-UHNVWZDZSA-N

物化性质

• 沸点：
  120 °C(Press: 0.2-0.3 Torr)
• 密度：
  1.291±0.06 g/cm3(Predicted)

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：

  (3S,4R)-tetrahydropyran-3,4-diol 在 吡啶 、 三甲基溴硅烷 、 二正丁基氧化锡 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 (3S,4R)-3-oleoyloxy-4-phosphoryloxytetrahydropyran
  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
• 作为产物：
  描述：

  L-(+)-arabinose 在 palladium on activated charcoal 、 氢溴酸 、 氢气 、 sodium methylate 、 sodium acetate 、 copper(II) acetate monohydrate 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 (3S,4R)-tetrahydropyran-3,4-diol
  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

文献信息

• Aspects of stereochemistry—I
  作者：J.S. Brimacombe、A.B. Foster、M. Stacey、D.H. Whiffen

  DOI：10.1016/0040-4020(58)80056-3

  日期：1958.1

  stabilities can be affected by hydrogen bonding from a substituent hydroxyl group to a ring oxygen. Additional evidence is provided in the case of the tetrahydropyran diols by [M]D values. The rate of reaction of the vicinal diols of these cyclic systems with glycol splitting reagents, and their zone electrophoretic mobility in an alkaline borate buffer is influenced by the presence of a ring oxygen.

  分子内氢键的如通过羟基拉伸区域红外光谱，在某些邻二醇确定的范围内，环己烷，环戊烷，四氢吡喃和四氢呋喃和相关化合物提供了用于不同的构象的稳定性的证据。在某些化合物中，这些稳定性可能会受到取代基羟基与环氧之间氢键的影响。对于四氢吡喃二醇，通过[ M ] D值提供了其他证据。这些环状体系的邻位二醇与二醇拆分剂的反应速率及其在碱性硼酸盐缓冲液中的区带电泳迁移率受环氧的影响。
• Chiroptical properties of tetrahydropyran-3,4-diols and 2-hydroxymethyltetrahydropyran-3-ols derived from l-arabinose, d-galactose, d-glucose, and d-xylose, and enantioselectivity in reduction with their complexes
  作者：Günther Snatzke、Zlata Raza、Ivan Habuš、Vitomir Šunjić

  DOI：10.1016/0008-6215(88)84002-3

  日期：1988.11

  lithium aluminium hydride has been studied. Low enantiomeric excess (⩽15%) was obtained, which was enhanced when an achiral modifier (ethanol, 2-propanol) was added to the complexes 10 and 11 prepared in situ . Enantioselective catalytic hydrogenation of Z -α-acetamidocinnamic acid was performed with the Rh(I)-norbornadiene complexes 2f and 4f , derived from the cis compounds 2a and 4a ; substantially

  摘要（3 R，4 R）-（1a）和（3 S，4 R）-四氢吡喃-3,4-二醇（2a）和（2 R，3 S）-（3a）和（2 R，3 R -2-羟甲基四氢吡喃-3-醇（4a），分别衍生自d-木糖，l-阿拉伯糖，d-葡萄糖和d-半乳糖，在结构上是最简单的双齿配体手性碳水化合物型前体。这些二醇与[Mo 2（OAc）4]以及苯甲酸酯（1b-4b）和甲苯磺酸酯（1c-4c）以及铜（I）配合物（1d-4d）之间的二齿配合物的cd光谱讨论了二苯基次膦酸酯（1e–4e）。研究了反式化合物1a和3a与氢化铝锂的配合物（分别为10和11）将苯乙酮对映选择性还原为S（R）-1-苯基乙醇。低的对映体过量（⩽15％），当将非手性改性剂（乙醇，2-丙醇）添加到就地制备的配合物10和11中时，其增强。用衍生自顺式化合物2a和4a的Rh（I）-降冰片二烯配合物2f和4f进行Z-α-乙酰氨基二甲酰胺酸的对映选择性催化加氢；对
• The Degradation of l-Arabinal to l-Erythrose¹
  作者：George E. Felton、Werner Freudenberg

  DOI：10.1021/ja01312a039

  日期：1935.9
• 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.