toluene-4-sulfonic acid (2'R,3'S)-3'-hydroxytetrahydropyran-2'-ylmethyl ester | 161946-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-sulfonic acid (2'R,3'S)-3'-hydroxytetrahydropyran-2'-ylmethyl ester
• 英文别名: toluene-4-sulfonic acid (2R,3S)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester；[(2R,3S)-3-hydroxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 161946-35-6
• 化学式: C₁₃H₁₈O₅S
• 分子量: 286.349
• InChiKey: YWWIPQFCDPSLDT-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid (2'R,3'S)-3'-hydroxytetrahydropyran-2'-ylmethyl ester 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 (2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)acetonitrile
  参考文献：
  名称：

  Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles

  摘要：

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.

  DOI：

  10.1021/jo9901438
• 作为产物：
  描述：

  ((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 toluene-4-sulfonic acid (2'R,3'S)-3'-hydroxytetrahydropyran-2'-ylmethyl ester
  参考文献：
  名称：

  的简明合成邻-condensed恶烷-oxene，oxepene，oxocene和oxonene环系统

  摘要：

  描述了一种有效的合成策略，该方法涉及包括硫代环化，随后的Ramberg-Bäcklund烯化为关键步骤的反式氧杂双环系统的合成。

  DOI：

  10.1016/0040-4039(96)00408-x

文献信息

• Tandem Alkylation−Michael Addition to Vinylogous Carbonates for the Stereoselective Construction of 2,3,3,6-Tetrasubstituted Tetrahydropyrans
  作者：Santosh J. Gharpure、S. Raja Bhushan Reddy

  DOI：10.1021/ol900721q

  日期：2009.6.18

  A stereoselective method for the synthesis of substituted tetrahydropyran derivatives employing a tandem SN2−Michael addition sequence to vinylogous carbonates is developed. The method is extended to the synthesis of bicyclic ether motifs present in polyether ladder toxins.

  开发了一种立体选择性的合成取代四氢吡喃衍生物的方法，该方法利用串联的S N 2-Michael加成序列到乙烯基碳酸酯。该方法扩展到聚醚梯形毒素中存在的双环醚基序的合成。
• Synthesis of novel sugar-lactam conjugates using the Aubé reaction
  作者：Suresh E. Kurhade、Tanaji Mengawade、Debnath Bhuniya、Venkata P. Palle、D. Srinivasa Reddy

  DOI：10.1039/c0ob00719f

  日期：——

  An efficient and convenient method for the synthesis of sugar-lactam conjugates is reported starting from readily available sugar azides using the Aubé reaction. Cyclic azido alcohols are used in the Aubé reaction for the first time in a carbohydrate setting. The resulting glycoconjugates could be further used to increase the chemical diversity on the sugar backbone, and may find potential applications as glycomimetics, peptidomimetics, in glycotargeting and in CNS drug delivery.

  报道了一种高效便捷的糖-内酰胺结合物合成方法，该方法以易得的糖叠氮化物为起始物，通过Aubé反应进行合成。环状叠氮醇首次被应用于碳水化合物领域的Aubé反应。所得到的糖结合物可以进一步用于增加糖主链的化学多样性，并可能在糖模拟物、肽模拟物、糖靶向以及中枢神经系统药物递送方面找到潜在应用。
• Simple Designs for the Construction of Complex Trans-Fused Polyether Toxin Frameworks. A Convergent Strategy Based on Hydroxy Ketone Cyclization of C-Linked Oxacycles
  作者：Eleuterio Alvarez、Ricardo Pérez、Milagros Rico、Rosa M. Rodríguez、Julio D. Martín

  DOI：10.1021/jo950547+

  日期：1996.1.1

  A single, unified convergent strategy for the stereocontrolled synthesis of trans-fused polyethers was developed. It was demonstrated that the epimerization and reductive intramolecular coupling of hydroxy ketones in reactions with silane-Lewis acids (SI-LA) to generate ethers in C-linked oxacycles is affected by its conformational preference in a predictable manner. The obtained results make evident

  开发了单一，统一的聚合策略，用于立体控制合成反式融合聚醚。结果表明，羟基酮与硅烷-路易斯酸（SI-LA）反应生成C-连接的氧杂环化合物中的醚，其差向异构化和还原性分子内偶联受其构象偏好的影响可预测。所得结果表明，半iketaltal羟基和1,3-双轴CO键之间的氢键的影响是规则的和可预测的，并且在热力学下驱动环闭合成恶烷环时，可以自信地进行反式稠合聚醚的收敛合成。条件
• Stereocontrolled intramolecular cyclization of ω-tributylstannyl ether aldehydes. synthesis of the 6·7·7·6 ring system of polycyclic ethers
  作者：Yoshinori Yamamoto、Jun-ichi Yamada、Isao Kadota

  DOI：10.1016/0040-4039(91)85042-4

  日期：1991.11

  γ-oxo-substituted allylic tin (1) having an aldehyde group at the terminus of the carbon chain proceeded in a stereocontrolled manner to give the 7-membered β-hydroxy cyclic ether (2a) with high diastereoselectivity. This method was applied for the synthesis of the 6·7·7·6 ring system (3a).

  BF 3 .OEt 2介导的在碳链末端具有醛基的γ-氧代取代的烯丙基锡（1）的分子内环化以立体控制的方式进行，得到了7元的β-羟基环醚（2a）高非对映选择性。该方法被用于6·7·7·6环系统（3a）的合成。