(3S)-5-[(2R,3R)-3-[2-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]pent-1-en-3-ol | 1437117-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-5-[(2R,3R)-3-[2-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]pent-1-en-3-ol
• CAS: 1437117-34-4
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: SVYVJGIOWKNJSH-FLDBGCDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-5-[(2R,3R)-3-[2-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]pent-1-en-3-ol 在 4-二甲氨基吡啶 、 Schwartz's reagent 、 四丙基高钌酸铵 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 氧气 、 碳酸氢钠 、 臭氧 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.25h， 生成 (2S,4aR,5aS,10aR,12aS)-2-((R)-4-((2S,3S,6R)-6-bromo-3-hydroxy-3,7,7-trimethyloxepan-2-yl)-2-hydroxybutan-2-yl)-5a,9,9,12a-tetramethyldecahydro-2H-oxepino[3,2-b]pyrano[2,3-f]oxepin-8(9H)-one
  参考文献：
  名称：

  Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades

  摘要：

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.041
• 作为产物：
  描述：

  5,9,13-trimethyl-4,8,12-tetradecatrienal 在 Oxone 、 Shi's ketone 、 四丁基硫酸氢铵 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 、 乙腈 为溶剂， 反应 19.33h， 生成 (3S)-5-[(2R,3R)-3-[2-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]pent-1-en-3-ol
  参考文献：
  名称：

  Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades

  摘要：

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.041

文献信息

• Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades
  作者：Brian S. Underwood、Jessica Tanuwidjaja、Sze-Sze Ng、Timothy F. Jamison

  DOI：10.1016/j.tet.2013.04.041

  日期：2013.6

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.