(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 | 261926-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 261926-74-3
• 化学式: C₆₃H₈₄O₁₄
• 分子量: 1065.35
• InChiKey: SQZSBWSKKQWDBB-JQFADIQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  77
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside 、 (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 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到(1S,3S,5R,6R,7S,8R,20S,22R,24R,25R,26S,27R,29S,31R,32R,33R)-5,24,31-trimethyl-33-[(2S,3R,4R,5S,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-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 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 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

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.