(S)-2-(Allyl-tert-butoxycarbonyl-amino)-3-benzyloxy-propionic acid | 220280-28-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-(Allyl-tert-butoxycarbonyl-amino)-3-benzyloxy-propionic acid
• 英文别名: (2S)-2-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]-3-phenylmethoxypropanoic acid
• CAS: 220280-28-4
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: SKWOQDXFLVWIAP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(Allyl-tert-butoxycarbonyl-amino)-3-benzyloxy-propionic acid 在 二异丁基氢化铝 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 3.67h， 生成 Allyl-((S)-2-benzyloxy-1-formyl-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors

  摘要：

  Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.

  DOI：

  10.1021/jo9815094
• 作为产物：
  描述：

  丙烯酰碘 、 N-BOC-O-苄基-L-丝氨酸 在 sodium hydride 作用下， 生成 2-(Allyl-tert-butoxycarbonyl-amino)-acrylic acid 、 (S)-2-(Allyl-tert-butoxycarbonyl-amino)-3-benzyloxy-propionic acid
  参考文献：
  名称：

  IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors

  摘要：

  Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.

  DOI：

  10.1021/jo9815094

文献信息

• IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors
  作者：Eliezer Falb、Yosi Bechor、Abraham Nudelman、Alfred Hassner、Amnon Albeck、Hugo E. Gottlieb

  DOI：10.1021/jo9815094

  日期：1999.1.1

  Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.