(3S,4S,5R,6S)-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidene-6-(trifluoroacetamido)piperidine-3-carboxylic acid | 153758-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3S,4S,5R,6S)-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidene-6-(trifluoroacetamido)piperidine-3-carboxylic acid
• 英文别名: (3S,4S,5R,6S)-1-(tert-butoxycarbonyl)-6-(trifluoroacetamido)-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid；(3R,4S,5R,6R)-3,4-isopropylidenedioxy-6-trifluoroacetamido-3-piperidinecarboxylic acid；(3aR,4S,7S,7aS)-2,2-dimethyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-4-[(2,2,2-trifluoroacetyl)amino]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-7-carboxylic acid
• CAS: 153758-24-8
• 化学式: C₁₆H₂₃F₃N₂O₇
• 分子量: 412.363
• InChiKey: GPLPVRWSEJPTHD-XKNYDFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R,6S)-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidene-6-(trifluoroacetamido)piperidine-3-carboxylic acid 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以97%的产率得到(3S,4S,5R,6R)-4,5-二羟基-6-[(2,2,2-三氟乙酰基)氨基]哌啶-3-羧酸
  参考文献：
  名称：

  由唾液抑素B实际合成的（3S，4S，5R，6R）-4,5-二羟基-6-（三氟乙酰胺基）哌啶-3-羧酸在小鼠中具有抗转移活性。

  摘要：

  DOI：

  10.1016/0008-6215(96)00052-3
• 作为产物：
  描述：

  (2S,3R,4S,5R)-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-O-isopropylidene-2-(trifluoroacetamido)-3,4-piperidinediol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到(3S,4S,5R,6S)-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidene-6-(trifluoroacetamido)piperidine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of the Sialidase Inhibitor Siastatin B

  摘要：

  The resolved piperidinecarboxylate (R)-7 was converted to siastatin B (1) by an efficient and stereoselective sequence that includes a bromo-beta -lactonization and an N-acyliminium azidation. Two analogues (3 and 4) of siastatin were also prepared.

  DOI：

  10.1021/ol0066680

文献信息

• Totally syntheticanalogues of siastatin B. III. Trifluoroacetamide analogues having inhibitory activity for tumor metastasis.
  作者：Yoshio NISHIMURA、Toshiaki KUDO、Shinichi KONDO、Tomio TAKEUCHI、TSUTOMU TSURUOKA、HARUMI FUKUYASU、SEUI SHIBAHARA

  DOI：10.7164/antibiotics.47.101

  日期：——

  A trifluoroacetamide analogue of siastatin B, (3R, 4R, 5R, 6R)-6-(trifluoroacetamido)-4, 5-dihydroxy-3-piperidinecarboxylic acid has been chemically synthesized. This compound, as well as the previously synthesized analogue, (3R, 4R, 5R, 6R)-6-(triiluoroacetamido)-3, 4, 5-trihydroxy-3-piperidinecarbo xylic acid, showed marked inhibitory activity against δ-glucuronidase and significant inhibition of experimental pulmonary metastasis of the highly metastatic melanoma B16.

  一种西司他丁 B 的三氟乙酰胺类似物--(3R, 4R, 5R, 6R)-6-(triluoroacetamido)-4, 5-二羟基-3-哌啶甲酸已被化学合成。该化合物以及之前合成的类似物 (3R，4R，5R，6R)-6-(三氟乙酰氨基)-3，4，5-三羟基-3-哌啶羧酸对δ-葡萄糖醛酸酶具有明显的抑制活性，并能显著抑制高度转移性黑色素瘤 B16 的实验性肺转移。
• A practical synthesis from siastatin B of (3S,4S,5R,6R)-4,5-dihydroxy-6-(trifluoroacetamido)piperidine-3-carboxylic acid having antimetastatic activity in mice
  作者：Takahiko Satoh、Yoshio Nishimura、Shinichi Kondo、Tomio Takeuchi

  DOI：10.1016/0008-6215(96)00052-3

  日期：1996.6
• Synthesis of the Sialidase Inhibitor Siastatin B
  作者：Spencer Knapp、Dalian Zhao

  DOI：10.1021/ol0066680

  日期：2000.12.1

  The resolved piperidinecarboxylate (R)-7 was converted to siastatin B (1) by an efficient and stereoselective sequence that includes a bromo-beta -lactonization and an N-acyliminium azidation. Two analogues (3 and 4) of siastatin were also prepared.