(4R,5R)-(5-allyl-2,2-dimethyl[1,3]dioxolan-4-yl)methanol | 852288-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-(5-allyl-2,2-dimethyl[1,3]dioxolan-4-yl)methanol
• 英文别名: (4R,5R)-2,2-dimethyl-5-(prop-2-en-1-yl)-1,3-dioxolan-4-methanol；[(4R,5R)-2,2-dimethyl-5-prop-2-enyl-1,3-dioxolan-4-yl]methanol
• CAS: 852288-61-0
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: WIKASJVGNPYKDR-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-(5-allyl-2,2-dimethyl[1,3]dioxolan-4-yl)methanol 在 盐酸 、 4-二甲氨基吡啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (2R,3R,4R)-hept-6-ene-2,3,4-tri-O-acetate
  参考文献：
  名称：

  一种有效的立体选择性全合成Synargentolide A及其差向异构体

  摘要：

  有效地完成了涉及D的自然存在的α-吡喃酮（= 2 H-吡喃-2-酮）衍生物synargentolide A（1）及其差向异构体2的立体选择性全合成。酒石酸为起始原料，烯烃交叉复分解反应为关键步骤。

  DOI：

  10.1002/hlca.201000342
• 作为产物：
  描述：

  (E)-hexa-2,5-dien-1-ol 在 4-二甲氨基吡啶 、 potassium osmate(VI) 、 甲基磺酰胺 、 potassium carbonate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 7.25h， 生成 (4R,5R)-(5-allyl-2,2-dimethyl[1,3]dioxolan-4-yl)methanol
  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

• First Enantioselective Synthesis of (-)-(2<i>S</i>,6<i>S</i>)-(6-Ethyltetrahydropyran-2-yl)formic Acid
  作者：Mário L. Vasconcellos、Leandro S. M. Miranda、Bruno A. Meireles、Jerônimo S. Costa、Vera. L. Pereira

  DOI：10.1055/s-2005-863744

  日期：——

  the first enantioselective synthesis of (-)-(2S,6S)-(6-ethyltetrahydropyran-2-yl)formic acid (2) in five steps (30% overall yield, 87% ee), from the commercial chiral template (R)-2,3-isopropylideneglyceraldehyde (4). The two stereogenic centers in 2 were controlled by diastereoselective Barbier allylation of 4 in aqueous media and an efficient Prins cyclization reaction between 5 with propanal.

  我们在这封信中描述了 (-)-(2S,6S)-(6-乙基四氢吡喃-2-基) 甲酸 (2) 的第一次对映选择性合成，分五步（30% 总产率，87% ee），来自商业手性模板 (R)-2,3-异丙叉甘油醛 (4)。2 中的两个立体中心由 4 在水性介质中的非对映选择性 Barbier 烯丙基化和 5 与丙醛之间的有效 Prins 环化反应控制。
• Asymmetric Synthesis of the 1-epi Aglycon of the Cripowellins A and B
  作者：Dieter Enders、Achim Lenzen、Gerhard Raabe

  DOI：10.1002/anie.200500556

  日期：2005.6.13
• 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.
• An Efficient Stereoselective Total Synthesis of Synargentolide A and Its Epimer
  作者：Biswanath Das、Penagaluri Balasubramanyam、Boyapati Veeranjaneyulu、Gandolla Chinna Reddy

  DOI：10.1002/hlca.201000342

  日期：2011.5

  The stereoselective total synthesis of a naturally occurring α‐pyrone (=2H‐pyran‐2‐one) derivative, synargentolide A (1), and of its epimer 2 (with the originally proposed structure of synargentolide A) was efficiently accomplished involving D‐tartaric acid as the starting material and an olefin cross‐metathesis reaction as the key step.

  有效地完成了涉及D的自然存在的α-吡喃酮（= 2 H-吡喃-2-酮）衍生物synargentolide A（1）及其差向异构体2的立体选择性全合成。酒石酸为起始原料，烯烃交叉复分解反应为关键步骤。