(4S,6R)-4-[(2R)-but-3-en-2-yl]-2-methoxy-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide | 1018689-51-4

• 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: (4S,6R)-4-[(2R)-but-3-en-2-yl]-2-methoxy-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide
• 英文别名: (4S,6R)-4-[(2R)-but-3-en-2-yl]-2-methoxy-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-1,3,2λ5-dioxaphosphinane 2-oxide
• CAS: 1018689-51-4
• 化学式: C₁₈H₂₇O₆P
• 分子量: 370.383
• InChiKey: DSENZEAYDUYKMT-WAKYUQPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 、 咪唑 、 4-二甲氨基吡啶 、 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 (3R,5S,6S,7R,11R,E)-5,7,11-tris(methoxymethoxy)-6,9-dimethyl-3-(triisopropylsilyloxy)tetradec-8-en-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
• 作为产物：
  描述：

  、 Dimethylzinc 、 三甲基硅烷化重氮甲烷 在 氰化亚铜 、 lithium chloride 作用下， 以 四氢呋喃 、 甲苯 、 甲醇 、 乙醚 为溶剂， 以87%的产率得到(4S,6R)-4-[(2R)-but-3-en-2-yl]-2-methoxy-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-1,3,2lambda5-dioxaphosphinane 2-oxide
  参考文献：
  名称：

  A Multifaceted Phosphate Tether:  Application to the C15−C30 Subunit of Dolabelides A−D

  摘要：

  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.

  DOI：

  10.1021/ol8001865

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.