(4S,5R)-2,2-dimethyl-5-(2-oxopropyl)-1,3-dioxolane-4-carboxylic acid | 872831-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-2,2-dimethyl-5-(2-oxopropyl)-1,3-dioxolane-4-carboxylic acid
• CAS: 872831-90-8
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: ALWMXFLUKRQRAM-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-2,2-dimethyl-5-(2-oxopropyl)-1,3-dioxolane-4-carboxylic acid 在 2-fluoro-1-ethylpyridinium tetrafluoroborate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,5R)-N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-2,2-dimethyl-N-(2-phenylmethoxyethyl)-5-(2-trimethylsilyloxyprop-2-enyl)-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093
• 作为产物：
  描述：

  (-)-2,3-O-亚异丙基-D-苏力糖醇 在 咪唑 、 ruthenium trichloride 、 sodium periodate 、 四丁基氟化铵 、 碘 、 叔丁基锂 、 sodium hydride 、 三苯基膦 、 calcium carbonate 、 碘甲烷 作用下， 以 四氢呋喃 、 四氯化碳 、 六甲基磷酰三胺 、 乙二醇二甲醚 、 正己烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 14.83h， 生成 (4S,5R)-2,2-dimethyl-5-(2-oxopropyl)-1,3-dioxolane-4-carboxylic acid
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093

文献信息

• Asymmetric Total Synthesis of the 1-<i>e</i><i>pi</i>-Aglycon of the Cripowellins A and B
  作者：Dieter Enders、Achim Lenzen、Michael Backes、Carsten Janeck、Kelly Catlin、Marie-Isabelle Lannou、Jan Runsink、Gerhard Raabe

  DOI：10.1021/jo0518093

  日期：2005.12.1

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.