(R)-2-((4S,6R)-6-(5-(4-methoxybenzyloxy)pentyl)-2,2-dimethyl-1,3-dioxan-4-yl)propan-1-ol | 1303438-61-0

• 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: (R)-2-((4S,6R)-6-(5-(4-methoxybenzyloxy)pentyl)-2,2-dimethyl-1,3-dioxan-4-yl)propan-1-ol
• 英文别名: (2R)-2-[(4S,6R)-6-[5-[(4-methoxyphenyl)methoxy]pentyl]-2,2-dimethyl-1,3-dioxan-4-yl]propan-1-ol
• CAS: 1303438-61-0
• 化学式: C₂₂H₃₆O₅
• 分子量: 380.525
• InChiKey: RKOXPAWWTYNWBI-UIFIKXQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-((4S,6R)-6-(5-(4-methoxybenzyloxy)pentyl)-2,2-dimethyl-1,3-dioxan-4-yl)propan-1-ol 在 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 四丁基氟化铵 、 氢气 、 叔丁基锂 、 碳酸氢钠 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 正戊烷 为溶剂， 反应 15.17h， 生成 (2R,3S,7R,E)-2-((4S,6R)-2,2-dimethyl-6-(pent-4-enyl)-1,3-dioxan-4-yl)-5-methyl-7-(triethylsilyloxy)dec-4-en-3-ol
  参考文献：
  名称：

  Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach

  摘要：

  The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S-p)-5 and (R,R,R-p)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.

  DOI：

  10.1021/jo2003506
• 作为产物：
  描述：

  (1S,6S,8S)-8-vinyl-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide 在 sodium tetrahydroborate 、 四氧化锇 、 Hoveyda-Grubbs catalyst second generation 、 copper(I) cyanide di(lithium chloride) 、 2-硝基苯磺酰肼 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 14.75h， 生成 (R)-2-((4S,6R)-6-(5-(4-methoxybenzyloxy)pentyl)-2,2-dimethyl-1,3-dioxan-4-yl)propan-1-ol
  参考文献：
  名称：

  Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach

  摘要：

  The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S-p)-5 and (R,R,R-p)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.

  DOI：

  10.1021/jo2003506

文献信息

• Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach
  作者：Paul R. Hanson、Rambabu Chegondi、John Nguyen、Christopher D. Thomas、Joshua D. Waetzig、Alan Whitehead

  DOI：10.1021/jo2003506

  日期：2011.6.3

  The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S-p)-5 and (R,R,R-p)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.