2-脱氧-alpha-L-赤式吡喃糖 | 113890-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 2-脱氧-alpha-L-赤式吡喃糖
• 英文名称: 2-Deoxy-alpha-L-erythro-pentopyranose
• 英文别名: (2R,4R,5S)-oxane-2,4,5-triol
• CAS: 113890-34-9
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: ZVQAVWAHRUNNPG-MROZADKFSA-N

物化性质

• 沸点：
  332.1±42.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 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：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  allyl vinylacetate 在 K₂Os(OH)4 titanium(IV) isopropylate 、 potassium dihydrogenphosphate 、 Hydroquinone 1,4-phthalazinediyl diether 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 23.5h， 生成 2-脱氧-alpha-L-赤式吡喃糖
  参考文献：
  名称：

  Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis

  摘要：

  graphicGrubbs' RuCl2(=CHPh)(PCy3)(2) (catalyst 1) and RuCl2(=CHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the construction of beta,gamma-unsaturated delta-lactones containing various substitution patterns of methyl groups. Asymmetric dihydroxylation followed by reduction leads to 3,4-cis-dihydroxy-2,6-dideoxypyranoses, which have proven to play very important biological roles as key components of natural products.

  DOI：

  10.1021/ol026710m

文献信息

• Synthesis of sn-1 functionalized phospholipids as substrates for secretory phospholipase A2
  作者：Lars Linderoth、Günther H. Peters、Kent Jørgensen、Robert Madsen、Thomas L. Andresen

  DOI：10.1016/j.chemphyslip.2006.12.006

  日期：2007.3

  Secretory phospholipase A2 (sPLA2) represents a family of small water-soluble enzymes that catalyze the hydrolysis of phospholipids in the sn-2 position liberating free fatty acids and lysophospholipids. Herein we report the synthesis of two new phospholipids (1 and 2) with bulky allyl-substituents attached to the sn-1 position of the glycerol backbone. The synthesis of phospholipids 1 and 2 is based upon the construction of a key aldehyde intermediate 3 which locks the stereochemistry in the sn-2 position of the final phospholipids. The aldehyde functionality serves as the site for insertion of the allyl-substituents by a zinc mediated allylation. Small unilamellar liposomes composed of phospholipids 1 and 2 were subjected to sPLA2 activity measurements. Our results show that only phospholipid 1 is hydrolyzed by the enzyme. Molecular dynamics simulations revealed that the lack of hydrolysis of phospholipid 2 is due to steric hindrance caused by the bulky side chain of the substrate allowing only limited access of water molecules to the active site.
• Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis
  作者：Peter R. Andreana、Jason S. McLellan、Yongchen Chen、Peng George Wang

  DOI：10.1021/ol026710m

  日期：2002.10.1

  graphicGrubbs' RuCl2(=CHPh)(PCy3)(2) (catalyst 1) and RuCl2(=CHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the construction of beta,gamma-unsaturated delta-lactones containing various substitution patterns of methyl groups. Asymmetric dihydroxylation followed by reduction leads to 3,4-cis-dihydroxy-2,6-dideoxypyranoses, which have proven to play very important biological roles as key components of natural products.