benzyl (2S)-3-hydroxypent-4-en-2-ylcarbamate

• 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: benzyl (2S)-3-hydroxypent-4-en-2-ylcarbamate
• 英文别名: benzyl N-[(2S,3S)-3-hydroxypent-4-en-2-yl]carbamate
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: WSAPLTNVUATUDT-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-3-hydroxypent-4-en-2-ylcarbamate 在 Hoveyda-Grubbs catalyst second generation 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 ethyl (2E,4S,5S)-5-benzyloxycarbonylamino-4-methoxymethoxy-2-hexenoate
  参考文献：
  名称：

  Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases

  摘要：

  In this study we revealed that the addition of an N-phenylacetamide substituent to the C-1 position of 1-deoxyfuconojirimycin (DFJ) can lead to highly potent inhibitors of alpha-L-fucosidases. A structure-activity relationship study showed that a fluoro group on the phenyl ring greatly increased its potency and selectivity. In contrast the addition of two or three fluoro groups decreased their inhibition potency. Consequently, N-(2-fluorophenyl)-2 beta-DFJ acetamide (18j) was found to display very potent and selective inhibition of bovine kidney, rat epididymis, and human lysosome alpha-L-fucosidases, with IC50 value of 0.012, 0.044, and 0.0079 mu M respectively. It is noteworthy that our designed N-phenyL-2 beta-DFJ acetamide derivative exhibited about 18-fold stronger effects on human lysosomal alpha-L-fucosidase than original DFJ and it occupied the active-site of this enzyme. We therefore expect that this compound may find applications in new therapeutic trials against genetic deficiency disorders. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.028
• 作为产物：
  描述：

  benzyl (S)-1-oxopropan-2-ylcarbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 benzyl (2S)-3-hydroxypent-4-en-2-ylcarbamate
  参考文献：
  名称：

  简明全合成（+）-氨基甲酸

  摘要：

  我们在此报告了一种高效的对映体选择性合成（+）-氨基甲酸的方法，该方法以9个步骤为最长的线性序列，关键策略是基于交叉复分解（CM）反应的新序列以及随后形成的环化还原胺化反应哌啶环。

  DOI：

  10.1016/j.tetlet.2003.12.010

文献信息

• Imino Glycals via Ruthenium-Catalyzed RCM and Isomerization
  作者：Bernd Schmidt、Sylvia Hauke、Nino Mühlenberg

  DOI：10.1055/s-0033-1338615

  日期：——

  enamides via a ruthenium-catalyzed assisted tandem catalytic ring-closing metathesis–isomerization sequence. The sequence relies on the in situ transformation of a metathesis active Ru–carbene into an isomerization active Ru–hydride by addition of hydroxide as a chemical trigger. N-Allyl-N-homoallylamines were converted in one step into cyclic enamides via a ruthenium-catalyzed assisted tandem catalytic

  摘要 N-烯丙基-N-高烯丙基胺一步一步通过钌催化的辅助串联催化闭环复分解-异构化过程转化为环状酰胺。该序列依赖于通过添加氢氧化物作为化学触发物，将复分解活性Ru-卡宾原位转化为异构化活性Ru-氢化物。 N-烯丙基-N-高烯丙基胺一步一步通过钌催化的辅助串联催化闭环复分解-异构化过程转化为环状酰胺。该序列依赖于通过添加氢氧化物作为化学触发物，将复分解活性Ru-卡宾原位转化为异构化活性Ru-氢化物。
• Diastereoselective addition of vinylmagnesium halides to variously N-mono- and N,N-diprotected l-alaninals
  作者：Dorota Gryko、Zofia Urbańczyk-Lipkowska、Janusz Jurczak

  DOI：10.1016/s0957-4166(97)00558-2

  日期：1997.12

  Diastereoselective C-2-elongation processes of N-mono- 1a-c and N,N-diprotected 1d-f L-alaninals, using vinylmagnesium bromide and chloride, are described. A substantial difference between effects of the N-protecting groups replacing either one or two amino protons was observed. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases
  作者：Atsushi Kato、Toru Okaki、Syohei Ifuku、Kasumi Sato、Yuki Hirokami、Ren Iwaki、Akiko Kamori、Shinpei Nakagawa、Isao Adachi、Peter G. Kiria、Osamu Onomura、Daishiro Minato、Kenji Sugimoto、Yuji Matsuya、Naoki Toyooka

  DOI：10.1016/j.bmc.2013.08.028

  日期：2013.11

  In this study we revealed that the addition of an N-phenylacetamide substituent to the C-1 position of 1-deoxyfuconojirimycin (DFJ) can lead to highly potent inhibitors of alpha-L-fucosidases. A structure-activity relationship study showed that a fluoro group on the phenyl ring greatly increased its potency and selectivity. In contrast the addition of two or three fluoro groups decreased their inhibition potency. Consequently, N-(2-fluorophenyl)-2 beta-DFJ acetamide (18j) was found to display very potent and selective inhibition of bovine kidney, rat epididymis, and human lysosome alpha-L-fucosidases, with IC50 value of 0.012, 0.044, and 0.0079 mu M respectively. It is noteworthy that our designed N-phenyL-2 beta-DFJ acetamide derivative exhibited about 18-fold stronger effects on human lysosomal alpha-L-fucosidase than original DFJ and it occupied the active-site of this enzyme. We therefore expect that this compound may find applications in new therapeutic trials against genetic deficiency disorders. (C) 2013 Elsevier Ltd. All rights reserved.
• Concise total synthesis of (+)-carpamic acid
  作者：Stefan Randl、Siegfried Blechert

  DOI：10.1016/j.tetlet.2003.12.010

  日期：2004.2

  We report herein an efficient enantioselective synthesis of (+)-carpamic acid, with nine steps as the longest linear sequence, the key strategy being based on a novel sequence of a cross-metathesis (CM) reaction and a subsequent cyclizing reductive amination to form the piperidine ring.

  我们在此报告了一种高效的对映体选择性合成（+）-氨基甲酸的方法，该方法以9个步骤为最长的线性序列，关键策略是基于交叉复分解（CM）反应的新序列以及随后形成的环化还原胺化反应哌啶环。