Benzyl 2,3-anhydro-β-L-lyxopyranoside | 95066-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 2,3-anhydro-β-L-lyxopyranoside
• 英文别名: (1R,2S,5S,6R)-2-phenylmethoxy-3,7-dioxabicyclo[4.1.0]heptan-5-ol
• CAS: 95066-28-7
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: GOKFKMWTGYINLH-QCNOEVLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzyl 2,3-anhydro-β-L-lyxopyranoside 在 1,1,3,3-四甲基脲 、 lithium bromide 作用下， 以 甲苯 为溶剂， 反应 0.13h， 以16%的产率得到(-)-(2S)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde
  参考文献：
  名称：

  Chiral aldehydes by ring contraction of pento- and hexopyranoside epoxides

  摘要：

  DOI：

  10.1021/jo00307a017
• 作为产物：
  描述：

  苄基 2,3-脱水-alpha-D-核吡喃糖苷 在 吡啶 、 sodium hydroxide 、 水 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 Benzyl 2,3-anhydro-β-L-lyxopyranoside
  参考文献：
  名称：

  Regioselective and stereoselective oxirane ring-openings of 2,3-anhydropentopyranosides with some methyl-group donating organometallic reagents

  摘要：

  DOI：

  10.1021/jo00254a023

文献信息

• An efficient route to regio- and stereoselective synthesis of 3-amino-3-deoxy sugars
  作者：Taleb H. Al-Tel、Raed A. Al-Qawasmeh、Christoph Schröder、Wolfgang Voelter

  DOI：10.1016/0040-4020(95)00087-o

  日期：1995.3

  Starting from the trans-oriented hydroxy-epoxy pentoses (1, 8 and 15) and benzoylisocyanate a regio- and stereoselective route via the benzoylcarbamate intermediates 2, 9 and 16 to the 3-amino-3-deoxy sugars 7, 14 and 18 is described.

  从反式-羟基-环氧戊糖（1、8和15）和苯甲酰基异氰酸酯开始，通过苯甲酰基氨基甲酸酯中间体2、9和16的区域和立体选择路线为3-氨基-3-脱氧糖7、14和18。描述。
• Classical synthesis of a new class of compounds via coupling of sugars and amino acids
  作者：Abdul Malik、Wolfgang Kowollik、Peter Scheer、Nighat Afza、Wolfgang Voelter

  DOI：10.1039/c39840001229

  日期：——

  A new class of pharmacologically interesting compounds has been synthesized through a novel SN2 dispalcement of the CF3SO2 group in benzyl 2,3-anhydro-4-trifluoromethylsulphonyl-α-D-ribopyranoside (1) and its β-L-isomer (2), by a variety of suitably protected naturally occurring amino acids: the reaction pathway also provides an efficient route to benzyl 2,3-anhydro-β-L- and -α-D-lyxopyranosides [(3)

  一类新的药理学上感兴趣的化合物已经通过一种新颖的合成小号Ñ的CF 2 dispalcement 3 SO 2在苄基2,3-脱水-4-三氟甲基磺酰基- α- d -ribopyranoside（1）和它的β-大号-异构体（2），可以通过各种适当保护的天然存在的氨基酸来实现：反应途径还提供了通往2,3,3-脱水-β - L-和-α - D- lyxopyranosides [（3）和（4）的有效途径） 分别]。
• Synthesis and inhibition properties of a series of pyranose derivatives towards a Zn-metalloproteinase from Saccharomonospora canescens
  作者：Pavlina Dolashka-Angelova、Raid J. Abdel-Jalil、Raed A. Al-Qawasmeh、Nicolina Stambolieva、Wolfgang Voelter

  DOI：10.1016/j.carres.2010.07.038

  日期：2010.11

  The Zn-proteinase, isolated from Saccharomonospora canescens (NPS), shares many common features with thermolysin, but considerable differences are also evident, as far as the substrate recognition site is concerned. In substrates of general structure AcylAlaAlaPhe 4NA, this neutral proteinase cleaves only the arylamide bond (non-typical activity of Zn-proteinases), while thermolysin attacks the peptide bond Ala-Phe. Phosphoramidon is a powerful tight binding inhibitor for thermolysin and significantly less specific towards NPS. The K-i-values (65 mu M for NPS vs 0.034 mu M for thermolysin) differ nearly 2000-folds. This implies significant differences in the specificity of the corresponding subsites. The carbohydrate moiety is supposed to accommodate in the S-1-subsite and the series of arabinopyranosides and glucopyranosides (12 compounds), which are assayed as inhibitors in a model system: NPS with SucAlaAlaPhe4NA as a substrate could be considered as mapping the S-1-subsite of NPS. Members of the series with an additional ring (3,4-epithio, 3,4-anhydro-derivatives) turned out to be reasonably good competitive inhibitors (K-i approximate to 0.1-0.2 mM are of the same order as the value for phosphoramidon). The structure of these compounds (8, 9, 11 and 12) seems to fit the size of the S-1-subsite and due to an appropriately oriented OH-group in addition, to protect the active site Zn2+. (C) 2010 Published by Elsevier Ltd.
• Zarga, Musa H. Abu; Al-Tel, Taleb H.; Voelter, Wolfgang, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1995, vol. 50, # 4, p. 697 - 698
  作者：Zarga, Musa H. Abu、Al-Tel, Taleb H.、Voelter, Wolfgang

  DOI：——

  日期：——
• Latif, Farzana; Malik, Abdul; Voelter, Wolfgang, Liebigs Annalen der Chemie, 1987, p. 617 - 620
  作者：Latif, Farzana、Malik, Abdul、Voelter, Wolfgang

  DOI：——

  日期：——