(2S*,3R*)-2-(2-hydroxyethyl)-3-hydroxytetrahydropyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S*,3R*)-2-(2-hydroxyethyl)-3-hydroxytetrahydropyran
• 英文别名: trans-2-(6-hydroxy-2-oxacyclohexyl)ethanol；(+/-)-trans-2-(2-hydroxyethyl)-2,3,5,6-tetrahydro-4H-pyran-3-ol；(2S,3R)-2-(2-hydroxyethyl)oxan-3-ol
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: NGMZWEOGUANFOE-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S*,3R*)-2-(2-hydroxyethyl)-3-hydroxytetrahydropyran 在 mercury(II) diacetate 咪唑 、 4-二甲氨基吡啶 、 pyridine-SO3 complex 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 159.0h， 生成
  参考文献：
  名称：

  闭环易位和烯醇醚的硼氢化反应合成海洋多环醚的亚单元

  摘要：

  已经探索了通过连续的闭环易位和烯醇醚的立体选择性氢硼化来构建多环醚。该反应序列已用于制备与在短毒素和相关海洋天然产物中发现的亚单位相对应的双环醚。

  DOI：

  10.1016/s0040-4020(99)00303-8
• 作为产物：
  描述：

  2-(3,4-Dihydro-2H-pyran-6-yl)ethan-1-ol 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以4.69 g的产率得到(2S*,3R*)-2-(2-hydroxyethyl)-3-hydroxytetrahydropyran
  参考文献：
  名称：

  闭环易位和烯醇醚的硼氢化反应合成海洋多环醚的亚单元

  摘要：

  已经探索了通过连续的闭环易位和烯醇醚的立体选择性氢硼化来构建多环醚。该反应序列已用于制备与在短毒素和相关海洋天然产物中发现的亚单位相对应的双环醚。

  DOI：

  10.1016/s0040-4020(99)00303-8

文献信息

• The furan approach to oxacycles. Part 3: Stereoselective synthesis of 2,3-disubstituted tetrahydropyrans
  作者：David Alonso、Manuel Pérez、Generosa Gómez、Berta Covelo、Yagamare Fall

  DOI：10.1016/j.tet.2005.01.001

  日期：2005.2

  Commercially available furan 1 was converted to 2,3-trans and 2,3-cis-disubstituted tetrahydropyrans 2 and 3 using a highly efficient route to oxacycles, based on the oxidation of the furan ring with singlet oxygen. Tetrahydropyrans 2 and 3 could be easily separated by column chromatography.

  基于呋喃环被单线态氧的氧化，使用高效的途径将可商购的呋喃1转化为2，3-反式和2，3-顺式-二取代的四氢吡喃2和3。四氢吡喃2和3可以通过柱色谱法轻松分离。
• A stereoselective synthesis of medium-sized cyclic ethers by the intramolecular cyclization of linear hydroxyalkyl-propargylic alcohols assisted by Co2(CO)8
  作者：JoséM Palazón、Victor S Martín

  DOI：10.1016/0040-4039(95)00555-q

  日期：1995.5

  A highly efficient, mild and general cyclization reaction of hydroxy exo-(propargyl)Co2(CO)6 cations leading to medium-sized (6 to 9 membered) cyclic ethers is described. The reaction is highly stereoselective when defined stereocenters are encountered in the linear precursor, providing a way to obtain fused cyclic ethers in their enantiomeric forms.

  描述了羟基外-（炔丙基）Co 2（CO）6阳离子的高效，温和且通用的环化反应，导致中等大小（6至9元）的环状醚。当在线性前体中遇到确定的立体中心时，该反应是高度立体选择性的，从而提供了一种以对映体形式获得稠合环状醚的方法。
• Stereoselective Synthesis of Novel Isonucleoside Analogues of Purine with a Tetrahydropyran Ring
  作者：Carmen Terán、Laura Estévez、Pedro Besada、Yagamare Fall、Marta Teijeira

  DOI：10.1055/s-0029-1217142

  日期：2010.2

  New tetrahydropyran isonucleoside derivatives of purine, with cis or trans configuration, were stereoselectively synthesized in moderate yield by a convergent strategy based on Mitsunobu coupling. The key starting material was a bicyclic lactone.

  通过一种基于三忍偶联的聚合策略，以中等收率立体选择性地合成了顺式或反式构型的新的四氢吡喃嘌呤异核苷衍生物。关键的起始材料是一种双环内酯。
• The furan approach to oxacycles: synthesis of medium-size 2,3-disubstituted oxacycles
  作者：Manuel Pérez、Pilar Canoa、Generosa Gómez、Carmen Terán、Yagamare Fall

  DOI：10.1016/j.tetlet.2004.05.035

  日期：2004.6

  We describe an efficient new approach for the synthesis of medium-size oxacycles that is based on the oxidation of a furan ring with singlet oxygen followed by an intramolecular Michael addition. This present study enlarges the scope of the furan approach strategy for the synthesis of oxepanes. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereocontrolled Synthesis of Cyclic Ethers by Intramolecular Hetero-Michael Addition. 5. Synthesis of All Diastereoisomers of 2,3,5,6-Tetrasubstituted Tetrahydropyrans
  作者：Juan M. Betancort、Víctor S. Martín、José M. Padrón、José M. Palazón、Miguel A. Ramírez、Marcos A. Soler

  DOI：10.1021/jo9619241

  日期：1997.7.1

  A systematic approach to the enantiomeric synthesis of all possible diastereoisomers of 2,6-dialkyl-3,5-dioxytetrahydropyrans is described. The key step in the described methodology is the intramolecular cyclization of enantiomerically enriched (greater than or equal to 95% ee) 7-hydroxy-4-(benzoyloxy)-2,3-unsaturated esters. Infused systems, six of the eight diastereoisomers for one enantiomeric series were synthesized using this procedure as a key step. Using those with the suitable stereochemistry, the two left were synthesized by simple chemical transformations: in one case by the basic isomerization of the carbon with the (methoxycarbonyl)methyl substituent or by a Mitsunobu inversion of a secondary alcohol available from the benzoyloxy group,in the remaining one by a consecutive sequence of oxidation and reduction reactions again over the free secondary alcohol. The stereochemistry of the intramolecular hetero-Michael addition leading to 2,3-disubstituted tetrahydropyrans is highly predictable when kinetic conditions (low temperature and sodium or potassium bases) are used and can be rationalized by invoking a model of a chair-like transition state in which the benzoyloxy group is located in the equatorial mode and the stereochemical course of the approach of the alpha,beta-unsaturated ester is controlled by the geometry of the double bond. As a rule of thumb, the cyclization using E double bonds yielded cis-2,3-disubstituted tetrahydropyrans, while (Z)-unsaturated esters yielded the trans compounds. This empirical rule is followed in highly substituted systems, leading to fused 2,3,5,6-tetrasubstituted tetrahydropyrans, with the same absolute configuration in the carbon where the nucleophilic oxygen is located and the one where the benzoyloxy group is located. Those systems having opposite configurations yield the same trans-2,3-disubstituted compound. The isomerization under thermodynamic conditions (room or higher temperature with excess of base) of the diastereoisomers with the (methoxycarbonyl)methyl substituent in the axial mode led quantitatively to those in which such a group was located equatorially. The scope and limitations of the method are described in both the synthesis of the unsaturated precursor and the stereochemistry reached in the cyclization step.