{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid butyl ester | 210293-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid butyl ester
• 英文别名: butyl 2-[(4R,6R)-6-[(1E,3E,8R)-8-[tert-butyl(dimethyl)silyl]oxynona-1,3-dienyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate
• CAS: 210293-65-5
• 化学式: C₂₇H₅₀O₅Si
• 分子量: 482.776
• InChiKey: UOQOZRIEDHCLCE-TUWWCLQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid butyl ester 在 tris-(dibenzylideneacetone)dipalladium(0) N-甲基吡咯烷酮 、 4-二甲氨基吡啶 、 18-冠醚-6 、 Dowex-H⁽¹⁺⁾ 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 macrolactin A
  参考文献：
  名称：

  Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions

  摘要：

  A highly convergent total synthesis of macrolactin A (1) utilizes modern asymmetric catalytic C-C coupling methods. The longest linear sequence in the route is 16 steps with an average yield of 86% per step. This total synthesis is valuable, because 1, which has been shown to possess activity against HIV, is not readily accessible from its natural source, a taxonomically unclassified deep-sea bacterium.

  DOI：

  10.1002/(sici)1521-3773(19980518)37:9<1261::aid-anie1261>3.0.co;2-2
• 作为产物：
  描述：

  (R)-3-((tert-butyldimethylsilyl)oxy)-1-iodobutane 在 tris-(dibenzylideneacetone)dipalladium(0) chromium dichloride 、 臭氧 、 N,N-二异丙基乙胺 、 cadmium(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 {(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid butyl ester
  参考文献：
  名称：

  Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions

  摘要：

  A highly convergent total synthesis of macrolactin A (1) utilizes modern asymmetric catalytic C-C coupling methods. The longest linear sequence in the route is 16 steps with an average yield of 86% per step. This total synthesis is valuable, because 1, which has been shown to possess activity against HIV, is not readily accessible from its natural source, a taxonomically unclassified deep-sea bacterium.

  DOI：

  10.1002/(sici)1521-3773(19980518)37:9<1261::aid-anie1261>3.0.co;2-2

文献信息

• Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions
  作者：Yuntae Kim、Robert A. Singer、Erick M. Carreira

  DOI：10.1002/(sici)1521-3773(19980518)37:9<1261::aid-anie1261>3.0.co;2-2

  日期：1998.5.18

  A highly convergent total synthesis of macrolactin A (1) utilizes modern asymmetric catalytic C-C coupling methods. The longest linear sequence in the route is 16 steps with an average yield of 86% per step. This total synthesis is valuable, because 1, which has been shown to possess activity against HIV, is not readily accessible from its natural source, a taxonomically unclassified deep-sea bacterium.