(4S,5R,6S)-4-allyl-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxane | 882491-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R,6S)-4-allyl-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxane
• 英文别名: (4S,5R,6S)-4-[(2R,3S)-3-methoxybutan-2-yl]-2,2,5-trimethyl-6-prop-2-enyl-1,3-dioxane
• CAS: 882491-70-5
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: DOVPBHYMSCJFAM-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  (4S,5R,6S)-4-allyl-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxane 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以81%的产率得到2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethanol
  参考文献：
  名称：

  Enantioselective Total Synthesis of FD-891

  摘要：

  The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits.

  DOI：

  10.1021/ja060018v
• 作为产物：
  描述：

  (2R,3S)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-hydroxy-2-methylhex-5-en-1-one 在 咪唑 、 2,6-二甲基吡啶 、 盐酸 、 sodium tetrahydroborate 、 cerium(III) chloride 、 四氯化钛 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 103.83h， 生成 (4S,5R,6S)-4-allyl-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxane
  参考文献：
  名称：

  Enantioselective Total Synthesis of FD-891

  摘要：

  The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits.

  DOI：

  10.1021/ja060018v

文献信息

• Enantioselective Total Synthesis of FD-891
  作者：Michael T. Crimmins、Franck Caussanel

  DOI：10.1021/ja060018v

  日期：2006.3.1

  The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits.
• Stereoselective Total Synthesis of FD-891
  作者：J. S. Yadav、Sukant Kishore Das、G. Sabitha

  DOI：10.1021/jo302205t

  日期：2012.12.21

  FD-891, a structurally unique 16-membered macrolide having anticancer activity, was synthesized according to a strategy employing asymmetric allylation, Prins cyclization, cross-metathesis reaction, Yamaguchi lactonization, and Julia-Kocienski olefination.