2-脱氧-D-阿拉伯吡喃糖 | 113890-37-2

• 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-D-阿拉伯吡喃糖
• 英文名称: 2-deoxy-β-L-erythro-pentopyranoside
• 英文别名: 2-deoxy-L-ribose；beta-2-desoxy-L-ribose；2-Desoxy-D-ribose；(2S,4R,5S)-tetrahydropyran-2,4,5-triol；(2S,4R,5S)-oxane-2,4,5-triol
• CAS: 113890-37-2
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: ZVQAVWAHRUNNPG-WISUUJSJSA-N

物化性质

• 熔点：
  92-95 °C
• 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

• 作为反应物：
  描述：

  2-脱氧-D-阿拉伯吡喃糖 在 吡啶 、 盐酸 作用下， 反应 17.0h， 生成 methyl 2-deoxy-3,5-di-O-p-toluoyl-α-L-erythro-pentofuranose
  参考文献：
  名称：

  Improved Synthesis of 2-Deoxy-L-ribose

  摘要：

  Improved synthesis of 2-deoxy-L-ribose and the corresponding 2-deoxy-3,5-di-O-p-toluoyl-alpha-L-elythro-pentofuranosyl chloride are described from L-arabinose.

  DOI：

  10.1080/07328319908044612
• 作为产物：
  描述：

  甲基-L-吡喃阿拉伯糖苷 在 盐酸 、 偶氮二异丁腈 、 Amberlyst 15 (H⁺ form) 、 Ph₂SiH 、 水 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成 2-脱氧-D-阿拉伯吡喃糖
  参考文献：
  名称：

  Improved Synthesis of 2-Deoxy-L-ribose

  摘要：

  Improved synthesis of 2-deoxy-L-ribose and the corresponding 2-deoxy-3,5-di-O-p-toluoyl-alpha-L-elythro-pentofuranosyl chloride are described from L-arabinose.

  DOI：

  10.1080/07328319908044612

文献信息

• <scp>C‐Aryl</scp> Glycosylation via Interrupted Pummerer Rearrangement^†
  作者：Jiagen Li、Xuefeng Jiang

  DOI：10.1002/cjoc.202300308

  日期：2023.11

  enzymes. Herein, C-aryl glycosylation was established for the synthesis of 2-sulfur C-aryl glycals and 1,2-dihydrobenzofuran-fused C-aryl glycosides via interrupted Pummerer process, featured with sulfonium-tethered [3,3]-sigmatropic rearrangement between sulfoxide glycals and phenols. This protocol offers a broad substrate scope with diverse glycosyl and phenols. Dapagliflozin, Empagliflozin, and Ipragliflozin

  C-芳基糖苷由于其独特的抗酶水解特性，是药物发现中重要的碳水化合物衍生物。在此，建立了通过间断Pummerer法合成2-硫C-芳基糖醛和1,2-二氢苯并呋喃稠合C-芳基糖苷的C-芳基糖基化，其特征在于锍系链的[3,3 ] -σ重排亚砜糖醛和酚类。该实验方案提供了具有多种糖基和酚类的广泛底物范围。达格列净、恩格列净和伊格列净类似物分别是直接实现的。
• 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.
• 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.