(3aR,4R,6R,6aS)-6-amino-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-4-ol | 151527-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,6R,6aS)-6-amino-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-4-ol
• 英文别名: (3aR,4R,6R,6aS)-6-amino-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol；(1R,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol
• CAS: 151527-83-2
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: AXPYGRDXRLICKY-MVIOUDGNSA-N

物化性质

• 沸点：
  288.0±40.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6R,6aS)-6-amino-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-4-ol 在 吡啶 、 盐酸 、 三(二甲氨基)锍二氟三甲基硅酸 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 生成 (1S,2S,3R,5S)-3-(7-((1R,2S)-2-(3,4-difluorophenyl)cyclopropylamino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-yl)-5-fluorocyclopentane-1,2-diol
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclopentyl-triazolol-pyrimidine (CPTP) based P2Y12 antagonists

  摘要：

  In this Letter we describe SAR investigation on the cyclopentyl-triazolol-pyrimidine scaffold in pursuit of new oral P2Y(12) inhibitors. Different synthetic routes were developed for variations at the cyclopentyl core. Optimization finally led to compound 2d which was advanced into preclinical development based on better potency and safety profile in comparison to ticagrelor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.055
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 镍 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 21.0h， 生成 (3aR,4R,6R,6aS)-6-amino-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-4-ol
  参考文献：
  名称：

  Synthesis of (1R,2S,3R,4R)-2,3,4-trihydroxycyclopentylamine from D-ribonolactone

  摘要：

  将核糖内酯3转化为氨基三醇12的七步程序可以获得28%的总收率。

  DOI：

  10.1039/c39940000083

文献信息

• Synthesis of Aminocyclitols by Intramolecular Reductive Coupling of Carbohydrate Derived δ- and ε-Functionalized Oxime Ethers Promoted by Tributyltin Hydride or Samarium Diiodide
  作者：José Marco-Contelles、Pilar Gallego、Mercedes Rodríguez-Fernández、Noureddine Khiar、Christine Destabel、Manuel Bernabé、Angeles Martínez-Grau、Jose Luis Chiara

  DOI：10.1021/jo970987w

  日期：1997.10.1

  carbonyl-tethered oxime ethers promoted by samarium diiodide can be performed in a one-pot sequence, following a Swern oxidation step, allowing the direct transformation of hydroxyl-tethered oxime ethers into the corresponding aminocyclitols. Moreover, the resultant O-benzylhydroxylamine products of these cyclizations can be further reduced in situ with excess samarium diiodide, in the presence of water, to the

  据报道，一系列简单或多氧的肟醚经溴化，α，β-不饱和酯，醛或酮基进行了δ-或ε-官能化的分子内还原偶联。还研究了腈系醛的环化。这些还原偶联由氢化三丁基锡或二碘化sa促进。反应在温和的条件下进行，化学收率高，立体选择性高。当应用于衍生自碳水化合物的高度官能化的底物时，该方法可选择性进入具有不同区域和立体化学特征的对映体纯氨基环醇。特别地，由二碘化mar促进的羰基连接的肟醚的还原偶联反应可以在Swern氧化步骤之后按一锅法进行，允许将羟基束缚的肟醚直接转化为相应的氨基环醇。而且，这些环化的所得O-苄基羟胺产物可以在水存在下用过量的二碘化sa原位进一步还原为相应的氨基醇，并具有优异的收率。讨论了这些化合物的一些转化。
• Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates
  作者：José Marco-Contelles、Pilar Ruiz、Luis Martínez、Angeles Martínez-Grau

  DOI：10.1016/s0040-4020(01)81837-8

  日期：1993.7

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.
• Synthesis of (1R,2S,3R,4R)-2,3,4-trihydroxycyclopentylamine from D-ribonolactone
  作者：Anthony H. Ingall、Peter R. Moore、Stanley M. Roberts

  DOI：10.1039/c39940000083

  日期：——

  A seven-step procedure for the transformation of ribonolactone 3 into the aminotriol 12 can be effected in 28% overall yield.

  将核糖内酯3转化为氨基三醇12的七步程序可以获得28%的总收率。
• Synthesis and biological evaluation of cyclopentyl-triazolol-pyrimidine (CPTP) based P2Y12 antagonists
  作者：Wangyang Tu、Jiang Fan、Haitang Zhang、Guoji Xu、Zhiwei Liu、Jian Qu、Fanglong Yang、Lei Zhang、Tianyu Luan、Jijun Yuan、Aishen Gong、Jun Feng、Piaoyang Sun、Qing Dong

  DOI：10.1016/j.bmcl.2013.11.055

  日期：2014.1

  In this Letter we describe SAR investigation on the cyclopentyl-triazolol-pyrimidine scaffold in pursuit of new oral P2Y(12) inhibitors. Different synthetic routes were developed for variations at the cyclopentyl core. Optimization finally led to compound 2d which was advanced into preclinical development based on better potency and safety profile in comparison to ticagrelor. (C) 2013 Elsevier Ltd. All rights reserved.