(2S,3S)-2-[(1E,3Z,5R,7E,9E,11R,12S,13R,14R,15S,17E)-14,19-bis[[tert-butyl(dimethyl)silyl]oxy]-3-ethyl-12-hydroxy-5,9,11,13,15,17-hexamethylnonadeca-1,3,7,9,17-pentaenyl]-3-methyl-2,3-dihydropyran-6-one | 217640-21-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,3S)-2-[(1E,3Z,5R,7E,9E,11R,12S,13R,14R,15S,17E)-14,19-bis[[tert-butyl(dimethyl)silyl]oxy]-3-ethyl-12-hydroxy-5,9,11,13,15,17-hexamethylnonadeca-1,3,7,9,17-pentaenyl]-3-methyl-2,3-dihydropyran-6-one
• CAS: 217640-21-6
• 化学式: C₄₅H₈₀O₅Si₂
• 分子量: 757.298
• InChiKey: ZXNNQKAPDFNIBF-WVHVYXBYSA-N

物化性质

• 沸点：
  729.5±60.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.54
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-[(1E,3Z,5R,7E,9E,11R,12S,13R,14R,15S,17E)-14,19-bis[[tert-butyl(dimethyl)silyl]oxy]-3-ethyl-12-hydroxy-5,9,11,13,15,17-hexamethylnonadeca-1,3,7,9,17-pentaenyl]-3-methyl-2,3-dihydropyran-6-one 在 吡啶 、 manganese(IV) oxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 、 戴斯-马丁氧化剂 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 生成 来普霉素B
  参考文献：
  名称：

  Absolute stereostructure and total synthesis of leptomycin B

  摘要：

  The absolute stereostructure of leptomycin B, an antitumor antibiotic and inhibitor of nuclear protein export, was firstly presumed as 1 having 4S, 5R, 10R, 16R, 18S, 19R, 20S on the basis of NMR comparison with callystatin A (2) and then 1 was asymmetrically synthesized. The synthesized leptomycin B (I) was found identical with the authentic sample in HPLC and CD comparison as well as in other respects. This structural elucidation of the absolute stereostructure and total synthesis are the first example;among the leptomycin family as Streptomyces metabolites. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01809-7
• 作为产物：
  描述：

  (2S,3S)-2-[(1E,3Z,5R)-3-ethyl-7-hydroxy-5-methylhepta-1,3-dienyl]-3-methyl-2,3-dihydropyran-6-one 在 dimsyl lithium 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (2S,3S)-2-[(1E,3Z,5R,7E,9E,11R,12S,13R,14R,15S,17E)-14,19-bis[[tert-butyl(dimethyl)silyl]oxy]-3-ethyl-12-hydroxy-5,9,11,13,15,17-hexamethylnonadeca-1,3,7,9,17-pentaenyl]-3-methyl-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Absolute stereostructure and total synthesis of leptomycin B

  摘要：

  The absolute stereostructure of leptomycin B, an antitumor antibiotic and inhibitor of nuclear protein export, was firstly presumed as 1 having 4S, 5R, 10R, 16R, 18S, 19R, 20S on the basis of NMR comparison with callystatin A (2) and then 1 was asymmetrically synthesized. The synthesized leptomycin B (I) was found identical with the authentic sample in HPLC and CD comparison as well as in other respects. This structural elucidation of the absolute stereostructure and total synthesis are the first example;among the leptomycin family as Streptomyces metabolites. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01809-7

文献信息

• Absolute stereostructure and total synthesis of leptomycin B
  作者：Motomasa Kobayashi、Weiqi Wang、Yasuhiro Tsutsui、Masanori Sugimoto、Nobutoshi Murakami

  DOI：10.1016/s0040-4039(98)01809-7

  日期：1998.11

  The absolute stereostructure of leptomycin B, an antitumor antibiotic and inhibitor of nuclear protein export, was firstly presumed as 1 having 4S, 5R, 10R, 16R, 18S, 19R, 20S on the basis of NMR comparison with callystatin A (2) and then 1 was asymmetrically synthesized. The synthesized leptomycin B (I) was found identical with the authentic sample in HPLC and CD comparison as well as in other respects. This structural elucidation of the absolute stereostructure and total synthesis are the first example;among the leptomycin family as Streptomyces metabolites. (C) 1998 Elsevier Science Ltd. All rights reserved.