Ethyl 2,3-dideoxy-4,5-O-isopropylidene-6-O-methanesulfonyl-L-erythro-hex-2-enoate | 149284-43-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 2,3-dideoxy-4,5-O-isopropylidene-6-O-methanesulfonyl-L-erythro-hex-2-enoate
• 英文别名: ethyl (E)-2,3-dideoxy-4,5-O-isopropylidene-6-O-methylsulfonyl-L-erythro-hex-2-enonate；((4S,5R)-5-((E)-2-(ethoxycarbonyl)vinyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate；ethyl (E)-3-[(4R,5S)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 149284-43-5
• 化学式: C₁₂H₂₀O₇S
• 分子量: 308.353
• InChiKey: DGGBPOWEWCWGFZ-YJOJJWFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 2,3-dideoxy-4,5-O-isopropylidene-6-O-methanesulfonyl-L-erythro-hex-2-enoate 在 sodium hydrogensulfide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 ethyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-6-thio-L-ribo-hexonate 、 ethyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-6-thio-L-arabino-hexonate
  参考文献：
  名称：

  Synthesis of five-membered homothiosugars derived from l-erythrose and d-mannose

  摘要：

  The synthesis of homothiosugars by conjugate addition of the hydrogen sulfide anion to the double bond of alpha,beta-unsaturated esters followed by nucleophilic internal displacement of a sulfonyloxy group is described. The new thiolanes were evaluated as enzyme inhibitors. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00365-1
• 作为产物：
  描述：

  2,3-O-isopropylidene-L-erythrofuranose 在 三(三苯基膦)羰基氢化铑 、 2,2,2-三氟乙醇 作用下， 以 甲苯 、 苯 为溶剂， 反应 192.0h， 生成 Ethyl 2,3-dideoxy-4,5-O-isopropylidene-6-O-methanesulfonyl-L-erythro-hex-2-enoate
  参考文献：
  名称：

  Stereoselective Synthesis of 4′-Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents

  摘要：

  Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5'-OH for phosphorylation, 4'-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5'-Homo-4'-selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity.

  DOI：

  10.1021/ol502899b

文献信息

• Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems
  作者：Deryk K. Thompson、Christine N. Hubert、Richard H. Wightman

  DOI：10.1016/s0040-4020(01)90234-0

  日期：1993.4

  Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octonate (23), could be converted in two steps into a beta-lactam.