(1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol | 138946-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol
• 英文别名: (3aR,4R,6R,6aS)-2,2-dimethyl-6-(phenylmethoxyamino)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 138946-55-1
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: BKSHDYFJBDJHQY-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 120.5h， 生成 (3aR,4S,6R,6aS)-6-氨基四氢-2,2-二甲基-4H-环戊烯并-1,3-二氧杂环戊烷-4-醇
  参考文献：
  名称：

  Synthesis and transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol: synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol

  摘要：

  The synthesis and some new transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol are described. Particularly relevant is the synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol 7 from D-ribonolactone, via intermediate 1, in eight steps and 12% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00236-x
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 20.0h， 生成 (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol
  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 (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 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。
• Carbocycles from carbohydrates. A free radical route to (1, 2, 3, 4)-4-Amino-1,2,3-cyclopentanetriol derivatives
  作者：José Marco-Contelles、Luis Martínez、Angeles Martínez Grau

  DOI：10.1016/s0957-4166(00)86136-4

  日期：1991.1

  Some derivatives of (1, 2, 3, 4)-4-Amino-1,2,3-cyclopentanetriol have been synthesized in enantiomerically pure form free radical cyclization of conveniently functionalized carbohydrate intermediates. Moderate yields and good to excellent diastereoselectivities have been obtained in the key intramolecular free radical cyclization step.

  的某些衍生物（1 ，2 ，3 ，4 ）-4-氨基-1,2,3- cyclopentanetriol已经在对映体纯形式合成方便地官能化碳水化合物的中间体的自由基环化。在关键的分子内自由基环化步骤中，已获得中等收率和良好至极好的非对映选择性。
• 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.
• Convenient syntheses of orthogonally protected aminocyclopentitols from aldopentoses
  作者：Urban Košak、Martina Hrast、Damijan Knez、Nenad Maraš、Martin Črnugelj、Stanislav Gobec

  DOI：10.1016/j.tetlet.2014.12.008

  日期：2015.1

  Orthogonally protected aminocyclopentitols were synthesized from commercially available aldopentoses using a convenient three-step procedure that does not require protection of the free anomeric hydroxyl group of the starting carbohydrate. The synthesized compounds are important building blocks with potential use in medicinal chemistry and drug discovery. (C) 2014 Elsevier Ltd. All rights reserved.