2-deoxy-4,5-O-isopropylidene-D-erythro-pent-1-enose diethyl dithioacetal | 64722-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-4,5-O-isopropylidene-D-erythro-pent-1-enose diethyl dithioacetal
• 英文别名: 1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-prop-2-en-1-ol；(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,3-bis(ethylsulfanyl)prop-2-en-1-ol
• CAS: 64722-92-5
• 化学式: C₁₂H₂₂O₃S₂
• 分子量: 278.437
• InChiKey: OKJOYKNWZGFQBD-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-deoxy-4,5-O-isopropylidene-D-erythro-pent-1-enose diethyl dithioacetal 在 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 sodium hexamethyldisilazane 、 silver nitrate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 44.42h， 生成 (2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-undecene-1,2,3-triol
  参考文献：
  名称：

  Cyclopropane-Containing Eicosanoids of Marine Origin. Biomimetic Synthesis of Constanolactones A and B from the Alga Constantinea simplex

  摘要：

  Asymmetric syntheses of 7, a substance isolated from incubation of arachidonic acid with an acetone powder of the coral Plexaura homomalla, and of constanolactones A (9) and B (10), metabolites of the red alga Constantinea simplex, are described. The key step involves stannic chloride-mediated cyclization of the oxirane derived from Sharpless epoxidation of 10-hydroxy-5,8-decadienoates, and is shown to yield a trans disubstituted cyclopropane Linked to a delta-lactone. Both (R) and (S) configurations at C5 of the lactone are produced in the cyclization, the ratio being independent of olefin geometry in the acyclic precursor, Elaboration of the cyclization products via Nozaki-Kishi coupling of the derived aldehydes 26 and 37 with the appropriate (1E,5Z)-1-iodo-1,5-undecadiene led to 7, 9, and 10, thereby establishing the relative configuration of 7 and confirming the absolute configuration of 9 and 10.

  DOI：

  10.1021/ja00128a008
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-D-arabinose diethyldithioacetal 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.0h， 以64%的产率得到2-deoxy-4,5-O-isopropylidene-D-erythro-pent-1-enose diethyl dithioacetal
  参考文献：
  名称：

  Cyclopropane-Containing Eicosanoids of Marine Origin. Biomimetic Synthesis of Constanolactones A and B from the Alga Constantinea simplex

  摘要：

  Asymmetric syntheses of 7, a substance isolated from incubation of arachidonic acid with an acetone powder of the coral Plexaura homomalla, and of constanolactones A (9) and B (10), metabolites of the red alga Constantinea simplex, are described. The key step involves stannic chloride-mediated cyclization of the oxirane derived from Sharpless epoxidation of 10-hydroxy-5,8-decadienoates, and is shown to yield a trans disubstituted cyclopropane Linked to a delta-lactone. Both (R) and (S) configurations at C5 of the lactone are produced in the cyclization, the ratio being independent of olefin geometry in the acyclic precursor, Elaboration of the cyclization products via Nozaki-Kishi coupling of the derived aldehydes 26 and 37 with the appropriate (1E,5Z)-1-iodo-1,5-undecadiene led to 7, 9, and 10, thereby establishing the relative configuration of 7 and confirming the absolute configuration of 9 and 10.

  DOI：

  10.1021/ja00128a008

文献信息

• Laulimalide Analogs and Uses Thereof
  申请人：Gallagher Jr M. Brian

  公开号：US20070287745A1

  公开（公告）日：2007-12-13

  The present invention provides compounds having formula I: and pharmaceutically acceptable derivatives thereof, wherein R 1 -R 10 , q, t, X 0 , X 1 , A, B, D, E, G, J, K, L, M and Z are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders associated with cellular hyperproliferation.

  本发明提供具有公式I的化合物及其药学上可接受的衍生物，其中R1-R10、q、t、X0、X1、A、B、D、E、G、J、K、L、M和Z如本文中一般和在类别和子类别中所述，并且此外还提供其药物组合物以及使用它们治疗与细胞过度增殖相关的疾病的方法。
• [EN] LAULIMALIDE ANALOGS WITH ANTI-CANCER ACTIVITITY<br/>[FR] ANALOGUES DE LAULIMALIDE ET UTILISATIONS DE CEUX-CI
  申请人：EISAI CO LTD

  公开号：WO2005030779A3

  公开（公告）日：2008-01-24