Ethyl 2,3-dideoxy-4,5-O-isopropylidene-6-O-methanesulfonyl-L-erythro-hex-2-enoate | 149284-44-6

• 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 (Z)-2,3-dideoxy-4,5-O-isopropylidene-6-O-methylsulfonyl-L-erythro-hex-2-enonate；((4S,5R)-5-((Z)-2-(ethoxycarbonyl)vinyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methylmethanesulfonate；ethyl (Z)-3-[(4R,5S)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 149284-44-6
• 化学式: C₁₂H₂₀O₇S
• 分子量: 308.353
• InChiKey: DGGBPOWEWCWGFZ-FACRAVRUSA-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 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 selenium 、 臭氧 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 121.0h， 生成 1,4-anhydro-5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-4-seleno-D-ribitol
  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
• 作为产物：
  描述：

  2,3-O-异亚丙基-d-赤藻糖 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Ethyl 2,3-dideoxy-4,5-O-isopropylidene-6-O-methanesulfonyl-L-erythro-hex-2-enoate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)90234-0

文献信息

• Synthesis of five-membered homothiosugars derived from l-erythrose and d-mannose
  作者：Jens Riedner、Inmaculada Robina、José G. Fernández-Bolaños、Silvia Gómez-Bujedo、José Fuentes

  DOI：10.1016/s0957-4166(99)00365-1

  日期：1999.8

  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.
• Stereoselective Synthesis of 4′-Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents
  作者：Pramod K. Sahu、Gyudong Kim、Jinha Yu、Ji Yoon Ahn、Jayoung Song、Yoojin Choi、Xing Jin、Jin-Hee Kim、Sang Kook Lee、Sunghyouk Park、Lak Shin Jeong

  DOI：10.1021/ol502899b

  日期：2014.11.7

  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.
• 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.