3,5-O-(S)-benzylidene-D-lyxono-1,4-lactone | 131614-82-9

• 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: 3,5-O-(S)-benzylidene-D-lyxono-1,4-lactone
• 英文别名: 3,5(S)-O-benzylidene-D-lyxono-1,4-lactone；3,5-O-benzylidene-D-lyxono-1,4-lactone；3,5-O-Benzyliden-D-lyxano-1,4-lacton；(2S,4aR,7S,7aR)-7-hydroxy-2-phenyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-6-one
• CAS: 131614-82-9
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: POQCVMCDQFBZKV-WDCWCFNPSA-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：

  3,5-O-(S)-benzylidene-D-lyxono-1,4-lactone 在 palladium on activated charcoal 吡啶 、 锂硼氢 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2S,3R,4S)-4-amino-1-benzyl-2-(hydroxymethyl)pyrrolidin-3-ol
  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 、 (3R,4S,5R)-3,4-二羟基-5-(羟基甲基)二氢-2(3H)-呋喃酮 在 盐酸 作用下， 以 水 为溶剂， 以90%的产率得到3,5-O-(S)-benzylidene-D-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

• Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones
  作者：So-Yeop Han、Madeleine M. Joullié、Valery V. Fokin、Nicos A. Petasis

  DOI：10.1016/s0957-4166(00)80400-0

  日期：1994.12

  D-xylonolactone, D-lyxonolactone 2-deoxy-D-ribonolactone toward benzaldehyde and acetone in acidic media, were examined. The reactions involved complex equilibria and were investigated with extensive 13C NMR studies as well as X-ray crystallographic analysis of selected products. Molecular mechanics (MM2) and semiempirical (PM3 and AM1) calculations of some derivatives were carried out in order to facilitate structural

  检查了D-核糖内酯，L-阿拉伯糖内酯，D-木糖内酯，D-苯二酸内酯2-脱氧-D-核糖内酯在酸性介质中对苯甲醛和丙酮的不同反应性。反应涉及复杂的平衡，并通过广泛的13 C NMR研究以及所选产品的X射线晶体学分析进行了研究。为了方便结构和构象的分配，对某些衍生物进行了分子力学（MM2）和半经验（PM3和AM1）计算。D-戊烯-1,4-内酯与苯甲醛和丙酮反应的反应活性差异在结构和构象方面均得到合理化。
• 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。
• Design and Synthesis of Orthogonally Protected <scp>d</scp>- and <scp>l</scp>-β-Hydroxyenduracididines from <scp>d</scp>-<i>lyxono</i>-1,4-Lactone
  作者：Cheng-Kun Lin、Chung-Chien Hou、Yi-Yong Guo、Wei-Chieh Cheng

  DOI：10.1021/acs.orglett.6b02444

  日期：2016.10.21

  A practical synthesis of the orthogonally protected d- and l-β-hydroxyenduracididines (d- and l-βhEnds), the unique, nonproteinogenic α-amino acids found in mannopeptimycin antibiotics, is described. We appropriately applied d-lyxono-1,4-lactone derivatives as a starting template and investigated two transformations: (i) reduction of the lactone in a two-step sequence and (ii) regioselective ring opening

  描述了一种实用合成的正交保护的d-和l -β-羟基神经尿苷（d-和l- βhEnds），这是在甘露肽霉素抗生素中发现的独特的，非蛋白原性的α-氨基酸。我们适当地将d - lyxono -1,4-内酯衍生物用作起始模板，并研究了两种转化：（i）以两步顺序还原内酯，以及（ii）亚苄基乙缩醛的区域选择性开环。通过仔细评估反应条件，成功制备了多克量的正交保护的d-和l- βhEnds。
• Synthesis from D-lyxonolactone of 1,4-Dideoxy-1,4-imino-L-arabinitol, a glucosidase inhibitor with in vitro anti-viral activity
  作者：James R. Behling、Arthur L. Campbell、Kevin A. Babiak、John S. Ng、John Medic、Payman Farid、George W.J. Fleet

  DOI：10.1016/s0040-4020(01)90163-2

  日期：1993.4

  Benzylidenation is the only protection required in a 7 step synthesis of the hydrochloride of 1,4-dideoxy-1,4-imino-L-arabinitol from D-lxyonolactone in an overall yield of 21%.
• Synthesis of the potent antiviral oxetane nucleoside epinoroxetanocin from D-lyxonolactone
  作者：Y. Wang、G.W.J. Fleet、R. Storer、P.L. Myers、C.J. Wallis、O. Doherty、D.J. Watkin、K. Vogt、D.R. Witty、F.X. Wilson、J.M. Peach

  DOI：10.1016/s0957-4166(00)80541-8

  日期：1990.1