(3S,5S)-6-[tert-butyl(diphenyl)silyl]oxy-3,5-dimethylhexan-1-amine | 320742-76-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3S,5S)-6-[tert-butyl(diphenyl)silyl]oxy-3,5-dimethylhexan-1-amine
• CAS: 320742-76-5
• 化学式: C₂₄H₃₇NOSi
• 分子量: 383.649
• InChiKey: XDDOJNGKWAQHSV-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,5S)-6-[tert-butyl(diphenyl)silyl]oxy-3,5-dimethylhexan-1-amine 在 氰基磷酸二乙酯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (R)-N-((3S,5S)-6-hydroxy-3,5-dimethylhexyl)-2-methylbutanamide
  参考文献：
  名称：

  Synthesis and Biological Activity of Kalkitoxin and its Analogues

  摘要：

  Total syntheses of kalkitoxin, isolated from the Caribbean Lyngbya majuscula, and its analogues, 3-epi-, 7-epi-, 8-epi-, 10-epi-, 10-nor-, and 16-nor-kalldtcocin, were achieved via oxazolidinone-based diastereoselective 1,4-addition reaction of a methyl group and efficient T1C14-mediated thiazoline ring formation as the key steps. The biological activities of synthetic kalkitoxin and its analogues were evaluated with brine shrimp.

  DOI：

  10.1021/jo201951s
• 作为产物：
  描述：

  (3S)-3-甲基-4-{[(2-甲基-2-丙基)(二苯基)硅烷基]氧基}丁醛 在 锂硼氢 、 sodium azide 、 溴化亚铜二甲硫醚 、 水 、 sodium hexamethyldisilazane 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.17h， 生成 (3S,5S)-6-[tert-butyl(diphenyl)silyl]oxy-3,5-dimethylhexan-1-amine
  参考文献：
  名称：

  Synthesis and Biological Activity of Kalkitoxin and its Analogues

  摘要：

  Total syntheses of kalkitoxin, isolated from the Caribbean Lyngbya majuscula, and its analogues, 3-epi-, 7-epi-, 8-epi-, 10-epi-, 10-nor-, and 16-nor-kalldtcocin, were achieved via oxazolidinone-based diastereoselective 1,4-addition reaction of a methyl group and efficient T1C14-mediated thiazoline ring formation as the key steps. The biological activities of synthetic kalkitoxin and its analogues were evaluated with brine shrimp.

  DOI：

  10.1021/jo201951s

文献信息

• An expeditious total synthesis of kalkitoxins: determination of the absolute stereostructure of natural kalkitoxin
  作者：Fumiaki Yokokawa、Toshinobu Asano、Tatsufumi Okino、William H. Gerwick、Takayuki Shioiri

  DOI：10.1016/j.tet.2004.06.014

  日期：2004.8

  Kalkitoxin, a potent neurotoxin isolated from the marine cyanobacteria Lyngbya majuscula, and its congeners (1–7) were efficiently synthesized utilizing Hruby's diastereoselective 1,4-addition and the Wipf's oxazoline-thiazoline conversion as key steps. These synthetic efforts in combination with spectral studies of natural kalkitoxin clearly determined the absolute stereostructure of kalkitoxin to

  Kalkitoxin，一种强效神经毒素从海洋蓝细菌分离鞘丝藻majuscula，其同类物（1 - 7）被有效地合成利用Hruby的非对映选择性1,4-加成和Wipf的恶唑啉噻唑啉转化为关键步骤。这些合成的努力与自然kalkitoxin的光谱研究相结合，明确确定kalkitoxin的绝对立体结构为7。
• Structure, Synthesis, and Biological Properties of Kalkitoxin, a Novel Neurotoxin from the Marine Cyanobacterium <i>Lyngbya </i><i>m</i><i>ajuscula</i>
  作者：Min Wu、Tatsufumi Okino、Lisa M. Nogle、Brian L. Marquez、R. Thomas Williamson、Namthip Sitachitta、Frederick W. Berman、Thomas F. Murray、Kevin McGough、Robert Jacobs、Kimberly Colsen、Toshinobu Asano、Fumiaki Yokokawa、Takayuki Shioiri、William H. Gerwick

  DOI：10.1021/ja005526y

  日期：2000.12.1
• Synthesis and Biological Activity of Kalkitoxin and its Analogues
  作者：Taiki Umezawa、Manabu Sueda、Takao Kamura、Teppei Kawahara、Xuerong Han、Tatsufumi Okino、Fuyuhiko Matsuda

  DOI：10.1021/jo201951s

  日期：2012.1.6

  Total syntheses of kalkitoxin, isolated from the Caribbean Lyngbya majuscula, and its analogues, 3-epi-, 7-epi-, 8-epi-, 10-epi-, 10-nor-, and 16-nor-kalldtcocin, were achieved via oxazolidinone-based diastereoselective 1,4-addition reaction of a methyl group and efficient T1C14-mediated thiazoline ring formation as the key steps. The biological activities of synthetic kalkitoxin and its analogues were evaluated with brine shrimp.