benzylidene-L-lyxono-1,4-lactone | 1021178-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: benzylidene-L-lyxono-1,4-lactone
• 英文别名: (2R,4aS,7R,7aS)-7-hydroxy-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-6-one
• CAS: 1021178-24-4
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: POQCVMCDQFBZKV-BTQIBKBOSA-N

物化性质

• 沸点：
  462.5±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  benzylidene-L-lyxono-1,4-lactone 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4aS,7S,7aS)-7-azido-2-phenyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one
  参考文献：
  名称：

  Efficient synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases

  摘要：

  The synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideOXY-L-arabinitoI LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-D-arabinitol DABNAc, was prepared from L-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhibitors Of D-hexosaminidase, whereas N-benzyl DABNAc exhibits weak competitive inhibition of the enzyme; this provides further evidence in support of Asano's hypothesis that while Dimino sugar mimics inhibit D-glycohydrolases competitively, their L-enantiomers show non-competitive inhibition and in the case of iminofuranoses L-enantiomers are usually more potent inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.041
• 作为产物：
  描述：

  苯甲醛 、 L-来苏糖酸-1,4-内酯 在 盐酸 作用下， 以 水 为溶剂， 生成 benzylidene-L-lyxono-1,4-lactone
  参考文献：
  名称：

  Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors

  摘要：

  摘要 2-乙酰氨基-1,4-亚氨基-1,2,4-三脱氧-D-核糖醇（DRBNAc）和对映体 LRBNAc 分别由 L- 和 D-lyxonolactone 制备而成，是潜在的己糖胺酸酶抑制剂。无论是 N-苄基-DRBNAc 还是 N-苄基-LRBNAc，都没有显示出对 α 或 β-己糖胺酶或任何其他糖苷酶的抑制作用。

  DOI：

  10.1016/j.crci.2010.03.020

文献信息

• High yield protection of alcohols, including tertiary and base sensitive alcohols, as benzhydryl ethers by heating with diphenyldiazomethane in the absence of any other reagent
  作者：Daniel Best、Sarah F. Jenkinson、Sebastian D. Rule、Rosemary Higham、Thomas B. Mercer、Richard J. Newell、Alexander C. Weymouth-Wilson、George W.J. Fleet、Sigthor Petursson

  DOI：10.1016/j.tetlet.2008.02.042

  日期：2008.3

  can be introduced efficiently without the need for any acid or base catalysis and which is not prone to acid or base catalysed migration is a significant advantage for many syntheses. Benzhydryl [diphenylmethyl] ethers of sugar lactones are formed in high yield under neutral conditions when the corresponding alcohol is heated with diphenyldiazomethane in an inert solvent such as acetonitrile or toluene;

  对于许多合成而言，可在不需要任何酸或碱催化的情况下有效地引入保护基且不易于被酸或碱催化的迁移的保护基是重要的优点。当相应的醇与二苯基重氮甲烷在惰性溶剂（如乙腈或甲苯）中加热时，在中性条件下，糖内酯的苄基[二苯基甲基]醚可以高收率形成；这样就可以在没有任何其他试剂的情况下轻松保护对碱敏感的和高度受阻的叔醇。
• Efficient synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases
  作者：J.S.Shane Rountree、Terry D. Butters、Mark R. Wormald、Raymond A. Dwek、Naoki Asano、Kyoko Ikeda、Emma L. Evinson、Robert J. Nash、George W.J. Fleet

  DOI：10.1016/j.tetlet.2007.04.041

  日期：2007.6

  The synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideOXY-L-arabinitoI LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-D-arabinitol DABNAc, was prepared from L-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhibitors Of D-hexosaminidase, whereas N-benzyl DABNAc exhibits weak competitive inhibition of the enzyme; this provides further evidence in support of Asano's hypothesis that while Dimino sugar mimics inhibit D-glycohydrolases competitively, their L-enantiomers show non-competitive inhibition and in the case of iminofuranoses L-enantiomers are usually more potent inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.
• Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors
  作者：J.S. Shane Rountree、Terry D. Butters、Raymond A. Dwek、George W.J. Fleet

  DOI：10.1016/j.crci.2010.03.020

  日期：2011.1

  Résumé 2-Acetamido-1,4-imino-1,2,4-trideoxy-D-ribitol (DRBNAc) and the enantiomeric LRBNAc were prepared as potential hexosaminidase inhibitors from L- and D-lyxonolactone, respectively. Neither N-benzyl-DRBNAc nor N-benzyl-LRBNAc showed any inhibition of α- or β-hexosaminidases or any other glycosidase.

  摘要 2-乙酰氨基-1,4-亚氨基-1,2,4-三脱氧-D-核糖醇（DRBNAc）和对映体 LRBNAc 分别由 L- 和 D-lyxonolactone 制备而成，是潜在的己糖胺酸酶抑制剂。无论是 N-苄基-DRBNAc 还是 N-苄基-LRBNAc，都没有显示出对 α 或 β-己糖胺酶或任何其他糖苷酶的抑制作用。