methyl (11S)-11-[(2R,3R,4R,5R,6R)-3-hydroxy-6-methyl-4,5-bis(phenylmethoxy)oxan-2-yl]oxytetradecanoate | 287945-08-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (11S)-11-[(2R,3R,4R,5R,6R)-3-hydroxy-6-methyl-4,5-bis(phenylmethoxy)oxan-2-yl]oxytetradecanoate
• CAS: 287945-08-8
• 化学式: C₃₅H₅₂O₇
• 分子量: 584.794
• InChiKey: GRJFGNCPLDCDRT-CBCULPSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  42
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (11S)-11-[(2R,3R,4R,5R,6R)-3-hydroxy-6-methyl-4,5-bis(phenylmethoxy)oxan-2-yl]oxytetradecanoate 在 4-二甲氨基吡啶 、 氢氧化钾 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 (1R,3S,5R,6R,7S,8R,20S,22R,24R,25R,26S,27R,29S,31R,32R,33R)-33-hydroxy-5,24,31-trimethyl-6,25,26,32-tetrakis(phenylmethoxy)-7-prop-2-enoxy-20-propyl-2,4,9,21,23,28,30-heptaoxatetracyclo[27.3.1.03,8.022,27]tritriacontan-10-one
  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：

  (11S)-11-hydroxytetradecanoic acid methyl ester 在 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (11S)-11-[(2R,3R,4R,5R,6R)-3-hydroxy-6-methyl-4,5-bis(phenylmethoxy)oxan-2-yl]oxytetradecanoate
  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.