(4S,5R)-5-Ethyl-2,2-dimethyl-1,3-dioxolan-4-carbonsaeure-ethylester | 85994-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-5-Ethyl-2,2-dimethyl-1,3-dioxolan-4-carbonsaeure-ethylester
• 英文别名: (2S,3R)-ethyl 2,3-isopropylidenedioxypentanoate；ethyl (4S,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 85994-57-6
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: GDVRTBXWVBHEKL-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-Ethyl-2,2-dimethyl-1,3-dioxolan-4-carbonsaeure-ethylester 在 二异丁基氢化铝 、 甲醇 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 D-苏-五糖,4,5-二脱氧-2,3-O-(1-甲基亚乙基)-(9CI)
  参考文献：
  名称：

  Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

  摘要：

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.018
• 作为产物：
  描述：

  (2S,3R)-ethyl-2,3-dihydroxypentanoate 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以98%的产率得到(4S,5R)-5-Ethyl-2,2-dimethyl-1,3-dioxolan-4-carbonsaeure-ethylester
  参考文献：
  名称：

  Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

  摘要：

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.018

文献信息

• USEFUL COMBINATIONS OF MONOBACTAM ANTIBIOTICS WITH BETA-LACTAMASE INHIBITORS
  申请人：Basilea Pharmaceutica AG

  公开号：US20150031662A1

  公开（公告）日：2015-01-29

  A pharmaceutical composition, comprising a combination of an antibiotically active compound of the formula (I): with a β-lactamase inhibitor of one of the formulae (II) to (XIII) are active against Gram-negative bacteria, in particular such bacteria which have become resistant against antibiotics such as aztreonam, carumonam and tigemonam. Optionally the compositions may comprise another β-lactamase inhibitor of one of the formulae (II) to (XIII), particularly of formula (V) or formula (VI).

  一种药物组合物，包括式(I)的抗生素活性化合物与式(II)至式(XIII)中的一种β-内酰胺酶抑制剂的组合，对革兰氏阴性菌有活性，特别是对已经对阿奇霉素、卡鲁莫纳和替莫纳等抗生素产生耐药性的细菌有活性。该组合物可以包括另一种式(II)至式(XIII)中的β-内酰胺酶抑制剂，特别是式(V)或式(VI)的β-内酰胺酶抑制剂。
• Hoffmann, Reinhard W.; Ladner, Wolfgang, Chemische Berichte, 1983, vol. 116, # 4, p. 1631 - 1642
  作者：Hoffmann, Reinhard W.、Ladner, Wolfgang

  DOI：——

  日期：——
• US9346799B2
  申请人：——

  公开号：US9346799B2

  公开（公告）日：2016-05-24