5-O-benzhydryl 1-O-tert-butyl (2S,3S)-2-acetamido-3-hydroxy-3,6-dihydro-2H-pyridine-1,5-dicarboxylate | 175721-63-8

• 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: 5-O-benzhydryl 1-O-tert-butyl (2S,3S)-2-acetamido-3-hydroxy-3,6-dihydro-2H-pyridine-1,5-dicarboxylate
• CAS: 175721-63-8
• 化学式: C₂₆H₃₀N₂O₆
• 分子量: 466.534
• InChiKey: PBMANNHQQBHIEC-GMAHTHKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-O-benzhydryl 1-O-tert-butyl (2S,3S)-2-acetamido-3-hydroxy-3,6-dihydro-2H-pyridine-1,5-dicarboxylate 在 吡啶 、 sodium tetrahydroborate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 mercury dichloride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.91h， 生成 (3R,4S,5S,6S)-6-acetamido-4-(N,N'-bis(tert-butoxycarbonyl)quanidino)-1-N-(tert-butoxycarbonyl)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine
  参考文献：
  名称：

  Synthesis and Antimetastatic Activity of l-Iduronic Acid-Type 1-N-Iminosugars

  摘要：

  L-Iduronic acid-type 1-N-iminosugars, (3R,4S,5R,6R)- and (3R,4S,5S,6R)-6-acetamido-4-amino-5-hydroxypiperidine-3-carboxylic acid (6 and 7, respectively), (3R,4S,5R,6R)-6-acetamido-4-guanidino-5-hydroxypiperidine-3-carboxylic acid (8), and (3R,4S,5R,6R)-4-amino- and -guanidino-5-hydroxy-6-(trifluoroacetamido)piperidin acid (9 and 10, respectively), were synthesized from siastatin B (1), isolated from Streptomyces culture, by the intramolecular Michael addition of O-imidate to its alpha,beta-unsaturated ester through cis oxiamination as a key step. Preincubation of B16 BL6 cells with these compounds inhibited invasion of the cells through reconstituted basement membranes. Pulmonary metastasis of B16 BL6 cells in mice was remarkably inhibited by pretreatment of the cells with these compounds in culture.

  DOI：

  10.1021/jm960627l
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-3,4-didehydro-4-deoxysiastatin B 、 二苯基重氮甲烷 以 甲醇 、 二氯甲烷 为溶剂， 以92%的产率得到5-O-benzhydryl 1-O-tert-butyl (2S,3S)-2-acetamido-3-hydroxy-3,6-dihydro-2H-pyridine-1,5-dicarboxylate
  参考文献：
  名称：

  Synthesis and Antimetastatic Activity of l-Iduronic Acid-Type 1-N-Iminosugars

  摘要：

  L-Iduronic acid-type 1-N-iminosugars, (3R,4S,5R,6R)- and (3R,4S,5S,6R)-6-acetamido-4-amino-5-hydroxypiperidine-3-carboxylic acid (6 and 7, respectively), (3R,4S,5R,6R)-6-acetamido-4-guanidino-5-hydroxypiperidine-3-carboxylic acid (8), and (3R,4S,5R,6R)-4-amino- and -guanidino-5-hydroxy-6-(trifluoroacetamido)piperidin acid (9 and 10, respectively), were synthesized from siastatin B (1), isolated from Streptomyces culture, by the intramolecular Michael addition of O-imidate to its alpha,beta-unsaturated ester through cis oxiamination as a key step. Preincubation of B16 BL6 cells with these compounds inhibited invasion of the cells through reconstituted basement membranes. Pulmonary metastasis of B16 BL6 cells in mice was remarkably inhibited by pretreatment of the cells with these compounds in culture.

  DOI：

  10.1021/jm960627l

文献信息

• The First <scp>l</scp>-Iduronic Acid-Type 1-<i>N</i>-Iminosugars Having Inhibitory Activity of Experimental Metastasis
  作者：Yoshio Nishimura、Takahiko Satoh、Hayamitsu Adachi、Shinichi Kondo、Tomio Takeuchi、Masayuki Azetaka、Harumi Fukuyasu、Yumiko Iizuka

  DOI：10.1021/ja953989b

  日期：1996.1.1