(2R,4S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxy-5-methyldecan-4-ol | 617714-98-4

• 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: (2R,4S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxy-5-methyldecan-4-ol
• 英文别名: (2R,4S,5S,8S)-8,10-bis[[tert-butyl(dimethyl)silyl]oxy]-1-[(2R,4S,6S)-4-[tert-butyl(diphenyl)silyl]oxy-6-[2-[(4-methoxyphenyl)methoxy]ethyl]oxan-2-yl]-2-methoxy-5-methyldecan-4-ol
• CAS: 617714-98-4
• 化学式: C₅₅H₉₂O₈Si₃
• 分子量: 965.587
• InChiKey: GFBAELLXXJIJNJ-SRDIXKJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.47
• 重原子数：
  66
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxy-5-methyldecan-4-ol 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 Schwartz's reagent 、 硼烷四氢呋喃络合物 、 2-甲基-2-丁烯 、 pyridine hydrofluoride 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 水 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 mineral oil 、 叔丁醇 、 苯 为溶剂， 反应 107.76h， 生成 (1R,3S,5S,7R,9R,13R,15S,18S)-7-hydroxy-3-methoxy-18-methyl-13-((E)-4-methylpent-1-enyl)-12,19,20-trioxatricyclo[13.3.1.1^5,9]icosan-11-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：

  (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 咪唑 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 N-甲基麻黄碱 、 水 、 1,8-双二甲氨基萘 、 L-Selectride 、 N-甲基吗啉氧化物 、 N-乙基苯胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 99.5h， 生成 (2R,4S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxy-5-methyldecan-4-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

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
• 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.