(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-hydroxy-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one | 918310-73-3

• 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: (2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-hydroxy-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one
• 英文别名: (2R,4S,7R,8R,9R,11R)-1-azido-9-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-2,4,11-trimethyl-7-triethylsilyloxy-14-trimethylsilyltetradec-13-yn-5-one
• CAS: 918310-73-3
• 化学式: C₃₂H₆₅N₃O₄Si₃
• 分子量: 640.142
• InChiKey: OEVAZWLIOQCXSK-AAPIXMJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.36
• 重原子数：
  42
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-hydroxy-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one 在 三乙基膦 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 (2R,3R,8R,10S)-2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-3-methyl-6-(trimethylsilyl)hex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane
  参考文献：
  名称：

  Antibodies with Broad Specificity to Azaspiracids by Use of Synthetic Haptens

  摘要：

  The development of general, sensitive, portable, and quantitative assays for the azaspiracid (AZA) class of marine toxins is urgently needed. Use of a synthetic hapten containing rings F-I of AZA to generate antibodies that cross-react with the AZAs via their common C28-C40 domain and use of these antibodies in ELISA and immunoaffinity columns are reported. This approach has many advantages over using intact azaspiracids (AZAs) derived from environmental samples or total synthesis as haptens for antibody development. A derivative of the levorotatory C28-C40 azaspiracid domain (1) was synthesized efficiently using a one-pot Staudinger reduction/intramolecular aza-Wittig reaction-imine capture sequence to form the H-I ring spiroaminal and a double intramolecluar hetero-Michael addition to assemble the F-G ring ketal. Conjugation of the hapten 1 to cBSA and immunization in sheep generated antibodies that recognized and bound to ovalbumin-conjugated 1 in the absence of AZA1. This binding was inhibited by 1 in a concentration-dependent manner. A mixture of AZA1, AZA2, AZA3, and AZA6 caused a degree of inhibition of antibody binding consistent with its total AZA content, rather than just its content of AZA1. This result suggests that the antibodies also have a similar affinity for AZA2, AZA3, and AZA6 as they do for AZA1 and that such antibodies are suitable for analysis of AZAs in shellfish samples.

  DOI：

  10.1021/ja066971h
• 作为产物：
  描述：

  (2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 草酰氯 、 pyridine-SO3 complex 、 sodium hexamethyldisilazane 、 甲基三辛基氯化铵 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 magnesium bromide 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 26.5h， 生成 (2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-hydroxy-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one
  参考文献：
  名称：

  Antibodies with Broad Specificity to Azaspiracids by Use of Synthetic Haptens

  摘要：

  The development of general, sensitive, portable, and quantitative assays for the azaspiracid (AZA) class of marine toxins is urgently needed. Use of a synthetic hapten containing rings F-I of AZA to generate antibodies that cross-react with the AZAs via their common C28-C40 domain and use of these antibodies in ELISA and immunoaffinity columns are reported. This approach has many advantages over using intact azaspiracids (AZAs) derived from environmental samples or total synthesis as haptens for antibody development. A derivative of the levorotatory C28-C40 azaspiracid domain (1) was synthesized efficiently using a one-pot Staudinger reduction/intramolecular aza-Wittig reaction-imine capture sequence to form the H-I ring spiroaminal and a double intramolecluar hetero-Michael addition to assemble the F-G ring ketal. Conjugation of the hapten 1 to cBSA and immunization in sheep generated antibodies that recognized and bound to ovalbumin-conjugated 1 in the absence of AZA1. This binding was inhibited by 1 in a concentration-dependent manner. A mixture of AZA1, AZA2, AZA3, and AZA6 caused a degree of inhibition of antibody binding consistent with its total AZA content, rather than just its content of AZA1. This result suggests that the antibodies also have a similar affinity for AZA2, AZA3, and AZA6 as they do for AZA1 and that such antibodies are suitable for analysis of AZAs in shellfish samples.

  DOI：

  10.1021/ja066971h