(2S,6R)-2-[(2R,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-methylenedecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-4-methylenetetrahydropyran | 617715-09-0

• 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: (2S,6R)-2-[(2R,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-methylenedecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-4-methylenetetrahydropyran
• CAS: 617715-09-0
• 化学式: C₄₁H₇₄O₆Si₂
• 分子量: 719.206
• InChiKey: MPAPPKXKRIMJFA-VCNDLIGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.28
• 重原子数：
  49.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2-[(2R,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-methylenedecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-4-methylenetetrahydropyran 在 sodium periodate 、 四氧化锇 、 水 、 L-Selectride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 丙酮 、 叔丁醇 为溶剂， 反应 33.5h， 生成 (2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-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
• 作为产物：
  描述：

  (2S,6R)-2-[1,3]dithian-2-ylmethyl-6-[2-(4-methoxybenzyloxy)ethyl]-4-methylenetetrahydropyran 在 水 、 1,8-双二甲氨基萘 、 calcium carbonate 、 碘甲烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.58h， 生成 (2S,6R)-2-[(2R,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-methylenedecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-4-methylenetetrahydropyran
  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

• Formal Synthesis of Leucascandrolide A
  作者：David R. Williams、Scott V. Plummer、Samarjit Patnaik

  DOI：10.1002/anie.200351817

  日期：2003.8.25