(2R,6S)-2-[(2S,5S,8S)-8,10-dihydroxy-2-methoxy-5-methyl-4-oxodecyl]-6-[2-[(4-methoxyphenyl)methoxy]ethyl]oxan-4-one | 1315479-97-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,6S)-2-[(2S,5S,8S)-8,10-dihydroxy-2-methoxy-5-methyl-4-oxodecyl]-6-[2-[(4-methoxyphenyl)methoxy]ethyl]oxan-4-one
• CAS: 1315479-97-0
• 化学式: C₂₇H₄₂O₈
• 分子量: 494.626
• InChiKey: MHEDDUDWBZWUEN-SNPZIINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,6S)-2-[(2S,5S,8S)-8,10-dihydroxy-2-methoxy-5-methyl-4-oxodecyl]-6-[2-[(4-methoxyphenyl)methoxy]ethyl]oxan-4-one 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 、
  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：

  (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 在 sodium periodate 、 四氧化锇 、 水 、 1,8-双二甲氨基萘 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 48.0h， 生成 、 (2R,6S)-2-[(2S,5S,8S)-8,10-dihydroxy-2-methoxy-5-methyl-4-oxodecyl]-6-[2-[(4-methoxyphenyl)methoxy]ethyl]oxan-4-one
  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

文献信息

• Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: applications for the synthesis of leucascandrolide A macrolactone
  作者：David R. Williams、Scott V. Plummer、Samarjit Patnaik

  DOI：10.1016/j.tet.2011.05.020

  日期：2011.7

  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.