(2R,3S)-2-(acetoxymethyl)tetrahydro-2H-pyran-3-yl acetate | 13391-23-6

• 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: (2R,3S)-2-(acetoxymethyl)tetrahydro-2H-pyran-3-yl acetate
• 英文别名: 4,6-Di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hexitol；4,6-Di-O-acetyl-1,5-anhydro-2,3-didesoxy-D-erythrohexit；4,6-Di-O-acetyl-1,5-anhydro-2,3-didesoxy-D-glucitol；Di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hexit；1,5-Anhydro-2,3-dideoxy-4,6-di-O-acetyl-D-glucitol；[(2R,3S)-3-acetyloxyoxan-2-yl]methyl acetate
• CAS: 13391-23-6
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: AZVXOOCCJLTFGJ-VHSXEESVSA-N

物化性质

• 沸点：
  285.9±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(acetoxymethyl)tetrahydro-2H-pyran-3-yl acetate 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium methylate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (2R,3S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl oleate
  参考文献：
  名称：

  Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity

  摘要：

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator that specifically activates membrane proteins of the P2Y and its related families of G protein coupled receptors (GPCR), GPR34 (LPS1), P2Y10 (LPS2), and GPR174 (LPS3). Here, in order to increase potency and receptor selectivity, we designed and synthesized LysoPS analogues containing the conformational constraints of the glycerol moiety. These reduced structural flexibility by fixation of the glycerol framework of LysoPS using a 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton, and related structures identified compounds which exhibited high potency and selectivity for activation of GPR34 or P2Y10. Morphing of the structural shape of the 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton into a planar benzene ring enhanced the P2Y10 activation potentcy rather than the GPR34 activation.

  DOI：

  10.1021/acs.jmedchem.5b01925
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 三乙基硅烷 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 (2R,3S)-2-(acetoxymethyl)tetrahydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity

  摘要：

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator that specifically activates membrane proteins of the P2Y and its related families of G protein coupled receptors (GPCR), GPR34 (LPS1), P2Y10 (LPS2), and GPR174 (LPS3). Here, in order to increase potency and receptor selectivity, we designed and synthesized LysoPS analogues containing the conformational constraints of the glycerol moiety. These reduced structural flexibility by fixation of the glycerol framework of LysoPS using a 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton, and related structures identified compounds which exhibited high potency and selectivity for activation of GPR34 or P2Y10. Morphing of the structural shape of the 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton into a planar benzene ring enhanced the P2Y10 activation potentcy rather than the GPR34 activation.

  DOI：

  10.1021/acs.jmedchem.5b01925

文献信息

• Oligophosphates with an antiviral action
  申请人：Bayer Aktiengesellschaft

  公开号：US05169842A1

  公开（公告）日：1992-12-08

  Novel oligophosphates with an antiviral action of the formula ##STR1## in which n is 3-50, B and E are, independently of one another, O, S or NH, A is O, NR or S, D is O, S or NR.sub.2, in which independently each R is H, alkyl, aralkyl or aryl, and X is --(CH.sub.2).sub.m --, ##STR2##

  具有抗病毒作用的新型寡磷酸盐的化学式为##STR1##其中n为3-50，B和E分别为O、S或NH，A为O、NR或S，D为O、S或NR.sub.2，其中独立的每个R为H、烷基、芳基烷基或芳基，X为--(CH.sub.2).sub.m --，##STR2##
• Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates
  作者：Kaname Sasaki、Takayuki Wakamatsu、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/j.tetlet.2006.09.091

  日期：2006.11

  A simple and easy method for chemoselective synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans from hex-2-enopyranosyl acetates was demonstrated. The former was achieved by hydrogenation catalyzed by Rh/Al2O3 in EtOAc/toluene solvent at 0 °C, while the latter was carried out using Pd/C in EtOH/AcOH at 25 °C.

  展示了一种简单易行的方法，用于从乙酸-2-烯并吡喃糖基乙酸酯化学选择性合成乙酸己吡喃酯基乙酸酯和2,3-二取代的四氢吡喃。前者是通过Rh / Al 2 O 3在EtOAc /甲苯溶剂中于0°C催化氢化而实现的，而后者是通过Pd / C在25°C的EtOH / AcOH中进行的。
• [EN] SMALL MOLECULE INHIBITORS OF GALECTIN-3<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE GALECTINE-3
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2019067702A9

  公开（公告）日：2019-04-25
• US5169842A
  申请人：——

  公开号：US5169842A

  公开（公告）日：1992-12-08