[(4R)-1-[tert-butyl(diphenyl)silyl]oxy-14-phenylmethoxytetradecan-4-yl] benzoate | 287945-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(4R)-1-[tert-butyl(diphenyl)silyl]oxy-14-phenylmethoxytetradecan-4-yl] benzoate
• CAS: 287945-04-4
• 化学式: C₄₄H₅₈O₄Si
• 分子量: 679.028
• InChiKey: KQUHGFQFBXANMU-RRHRGVEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  49
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4R)-1-[tert-butyl(diphenyl)silyl]oxy-14-phenylmethoxytetradecan-4-yl] benzoate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 四溴化碳 、 四丁基氟化铵 、 四丁基氯化铵 、 氨 、 三正丁基氢锡 、 sodium methylate 、 sodium 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (11S)-11-hydroxytetradecanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of calonyctin A2, a macrolidic glycolipid with plant growth-promoting activity

  摘要：

  Calonyctin A2, a tetrasaccharidic glycolipid having a 22-membered macrolidic structure, has been synthesized by the assembly of three 6-deoxygenated thioglycoside intermediates. The short-step synthesis was achieved by preparation of the most complicated b-c disaccharide unit from phenyl 2,2':4,6:4',6'-tri-O-benzylidene-1-thio-beta-D-laminaribioside without any glycosidation reaction and by regioselective macrolactonization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00427-5
• 作为产物：
  描述：

  (2S)-toluene-4-sulfonic acid 5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-pentyl ester 在 吡啶 、 copper(l) iodide 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 [(4R)-1-[tert-butyl(diphenyl)silyl]oxy-14-phenylmethoxytetradecan-4-yl] benzoate
  参考文献：
  名称：

  Total synthesis of calonyctin A2, a macrolidic glycolipid with plant growth-promoting activity

  摘要：

  Calonyctin A2, a tetrasaccharidic glycolipid having a 22-membered macrolidic structure, has been synthesized by the assembly of three 6-deoxygenated thioglycoside intermediates. The short-step synthesis was achieved by preparation of the most complicated b-c disaccharide unit from phenyl 2,2':4,6:4',6'-tri-O-benzylidene-1-thio-beta-D-laminaribioside without any glycosidation reaction and by regioselective macrolactonization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00427-5

文献信息

• Total synthesis of calonyctin A2, a macrolidic glycolipid with plant growth-promoting activity
  作者：Jun-ichi Furukawa、Shigeru Kobayashi、Motoyoshi Nomizu、Norio Nishi、Nobuo Sakairi

  DOI：10.1016/s0040-4039(00)00427-5

  日期：2000.4

  Calonyctin A2, a tetrasaccharidic glycolipid having a 22-membered macrolidic structure, has been synthesized by the assembly of three 6-deoxygenated thioglycoside intermediates. The short-step synthesis was achieved by preparation of the most complicated b-c disaccharide unit from phenyl 2,2':4,6:4',6'-tri-O-benzylidene-1-thio-beta-D-laminaribioside without any glycosidation reaction and by regioselective macrolactonization. (C) 2000 Elsevier Science Ltd. All rights reserved.