(5R,9R,10S,11S,13R,E)-15,15-diisopropyl-9,11-bis(methoxymethoxy)-7,10,16-trimethyl-13-(pent-4-enyl)-5-propyl-2,4,14-trioxa-15-silaheptadec-7-ene | 1018689-64-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (5R,9R,10S,11S,13R,E)-15,15-diisopropyl-9,11-bis(methoxymethoxy)-7,10,16-trimethyl-13-(pent-4-enyl)-5-propyl-2,4,14-trioxa-15-silaheptadec-7-ene
• 英文别名: tri(propan-2-yl)-[(6R,8S,9S,10R,11E,14R)-8,10,14-tris(methoxymethoxy)-9,12-dimethylheptadeca-1,11-dien-6-yl]oxysilane
• CAS: 1018689-64-9
• 化学式: C₃₄H₆₈O₇Si
• 分子量: 616.995
• InChiKey: GSGWHUGWQNKLON-KEBQMIAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  42
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4S,6R)-4-[(2R)-but-3-en-2-yl]-2-methoxy-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide 在 吡啶 、 三乙烯二胺 、 咪唑 、 4-二甲氨基吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 叔丁基锂 、 臭氧 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc dibromide 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 (5R,9R,10S,11S,13R,E)-15,15-diisopropyl-9,11-bis(methoxymethoxy)-7,10,16-trimethyl-13-(pent-4-enyl)-5-propyl-2,4,14-trioxa-15-silaheptadec-7-ene
  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

• A Multifaceted Phosphate Tether:  Application to the C15−C30 Subunit of Dolabelides A−D
  作者：Alan Whitehead、Joshua D. Waetzig、Christopher D. Thomas、Paul R. Hanson

  DOI：10.1021/ol8001865

  日期：2008.4.1

  Construction of the C15-C30 subunit of dolabelide utilizing a temporary phosphate tether is described. Two routes are reported that make use of the orthogonal protecting- and leaving-group properties innate to phosphate esters. One route relies on a selective terminal oxidation, while a second utilizes a CM/selective hydrogenation sequence. Both routes depend on a highly regio- and diastereoselective cuprate addition to set the requisite stereochemistry at C22.
• 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.