toluene-4-sulfonic acid (1S,5S)-6-[1,3]dithian-2-yl-5-hydroxy-1-[2-(4-methoxybenzyloxy)ethyl]-3-methylene-hexyl ester | 617715-05-6

• 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 (1S,5S)-6-[1,3]dithian-2-yl-5-hydroxy-1-[2-(4-methoxybenzyloxy)ethyl]-3-methylene-hexyl ester
• CAS: 617715-05-6
• 化学式: C₂₈H₃₈O₆S₃
• 分子量: 566.804
• InChiKey: DXTZEXGMDUGJGO-AZGAKELHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  37.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid (1S,5S)-6-[1,3]dithian-2-yl-5-hydroxy-1-[2-(4-methoxybenzyloxy)ethyl]-3-methylene-hexyl ester 在 水 、 sodium hydride 、 calcium carbonate 、 碘甲烷 作用下， 以 二氯甲烷 、 乙腈 、 mineral oil 、 苯 为溶剂， 反应 41.58h， 生成 (2R,5S,8S)-8,10-bis(tert-butyldimethylsilyloxy)-1-((2S,6R)-6-(2-(4-methoxybenzyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-5-methyl-4-methylenedecan-2-ol
  参考文献：
  名称：

  Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: applications for the synthesis of leucascandrolide A macrolactone

  摘要：

  Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in S-E' reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at -78 degrees C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone 2 via the sequential applications of S-E' reactions leading to the C-1-C-9 aldehyde 14, and the bis-tetrahydropyran 59, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.020
• 作为产物：
  描述：

  toluene-4-sulfonic acid (5S)-5-(tert-butyldimethylsilanyloxy)-6-[1,3]dithian-2-yl-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methylenehexyl ester 在 pyridine hydrofluoride 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以87%的产率得到toluene-4-sulfonic acid (1S,5S)-6-[1,3]dithian-2-yl-5-hydroxy-1-[2-(4-methoxybenzyloxy)ethyl]-3-methylene-hexyl ester
  参考文献：
  名称：

  Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: applications for the synthesis of leucascandrolide A macrolactone

  摘要：

  Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in S-E' reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at -78 degrees C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone 2 via the sequential applications of S-E' reactions leading to the C-1-C-9 aldehyde 14, and the bis-tetrahydropyran 59, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.020