(3aR,4R,7aS)-2,2,4-trimethyl-6-(1-phenylethenyl)-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran | 864444-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aR,4R,7aS)-2,2,4-trimethyl-6-(1-phenylethenyl)-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 864444-82-6
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: IIUKLKVGXVHOLU-UHOFOFEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7aS)-2,2,4-trimethyl-6-(1-phenylethenyl)-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran 在 咪唑 、 甲醇 、 AD-mix-α 、 硼烷四氢呋喃络合物 、 pyridine-SO3 complex 、 D(+)-10-樟脑磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 82.0h， 生成 (R)-[(3aR,4R,6S,7S,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-hydroxy-phenyl-acetaldehyde
  参考文献：
  名称：

  Synthesis of the Branched C-Glycoside Substructure of Altromycin B

  摘要：

  [GRAPHICS]Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b).

  DOI：

  10.1021/ol050975u
• 作为产物：
  描述：

  、 1-phenyl-1-iodoethylene 在 copper(l) iodide 、 四(三苯基膦)钯 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以66%的产率得到(3aR,4R,7aS)-2,2,4-trimethyl-6-(1-phenylethenyl)-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran
  参考文献：
  名称：

  Synthesis of the Branched C-Glycoside Substructure of Altromycin B

  摘要：

  [GRAPHICS]Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b).

  DOI：

  10.1021/ol050975u

文献信息

• Synthesis of 15,28-Dideoxy-15,28-didehydrothyrsenol
  作者：Frank E. McDonald、Mary A. Smart

  DOI：10.3987/com-12-s(n)51

  日期：——

  The tetracyclic skeleton of thyrsenols A and B has been assembled, with the construction of ring A by exo-selective oxacyclization of an epoxybromohydrin, B ring formation by exo-selective oxacyclization of hydroxyepoxide followed by solvolytic ring expansion of a tetrahydrofuran to tetrahydropyran, C ring closure by tungsten-promoted endo-selective oxacyclization of a hydroxyalkyne, and D ring preparation by asymmetric dihydroxylation of an epoxyalkene accompanied by exo-selective oxacyclization. A modified Stille coupling linked two fragments at C-14-C-15 to directly provide the tetracyclic dienylether.
• Synthesis of the Branched <i>C</i>-Glycoside Substructure of Altromycin B
  作者：Bonsuk Koo、Frank E. McDonald

  DOI：10.1021/ol050975u

  日期：2005.8.1

  [GRAPHICS]Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b).