(1R,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-1-methyl-4-oxo-cyclopentanecarbaldehyde | 357187-48-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-1-methyl-4-oxo-cyclopentanecarbaldehyde
• 英文别名: (1R,2S,3R)-2-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-1-methyl-4-oxocyclopentane-1-carbaldehyde
• CAS: 357187-48-5
• 化学式: C₁₄H₂₆O₄Si
• 分子量: 286.444
• InChiKey: RQNIOICSROMQDZ-SCRDCRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-1-methyl-4-oxo-cyclopentanecarbaldehyde 在 chromium dichloride 、 六甲基磷酰三胺 、 lithium hydroxide 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二甲基亚砜 为溶剂， 生成 (3R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-((E)-2-iodo-vinyl)-2,3-dimethoxy-5-methyl-cyclopent-1-enecarboxylic acid
  参考文献：
  名称：

  Studies directed toward the synthesis of viridenomycin. Route 2: a second generation approach

  摘要：

  A second generation approach toward the synthesis of viridenomycin is described. Three key fragments of the molecule have been synthesized in stereochemically pure form. Initial studies toward the coupling of these fragments with the aim of assembling the macrocycle are detailed. Final efforts to reach the title compound are documented. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00701-8
• 作为产物：
  描述：

  (2R,3S,4S)-3-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-4-methyl-4-(phenylmethoxymethyl)cyclopentan-1-one 在 palladium on activated charcoal N-甲基吲哚酮 、 四丙基高钌酸铵 、 氢气 作用下， 生成 (1R,2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-1-methyl-4-oxo-cyclopentanecarbaldehyde
  参考文献：
  名称：

  研究针对病毒霉素的合成。途径1：组装三种高级中间体

  摘要：

  已经制备了代表抗真菌抗生素viridenomycin片段的三个对映异构体和几何纯净的结构单元。

  DOI：

  10.1016/s0040-4039(01)00700-6

文献信息

• Studies directed toward the synthesis of viridenomycin. Route 2: a second generation approach
  作者：Alex G Waterson、Albert W Kruger、A.I Meyers

  DOI：10.1016/s0040-4039(01)00701-8

  日期：2001.6

  A second generation approach toward the synthesis of viridenomycin is described. Three key fragments of the molecule have been synthesized in stereochemically pure form. Initial studies toward the coupling of these fragments with the aim of assembling the macrocycle are detailed. Final efforts to reach the title compound are documented. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Studies directed toward the synthesis of viridenomycin. Route 1: assembly of three advanced intermediates
  作者：Albert W Kruger、A.I Meyers

  DOI：10.1016/s0040-4039(01)00700-6

  日期：2001.6

  Three enantiomerically and geometrically pure building blocks representing fragments of the antifungal antibiotic viridenomycin have been prepared.

  已经制备了代表抗真菌抗生素viridenomycin片段的三个对映异构体和几何纯净的结构单元。