Benzyl-2-O-p-toluolsulfonyl-3,4-O-isopropyliden-β-L-arabinopyranosid | 68753-33-3

• 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-2-O-p-toluolsulfonyl-3,4-O-isopropyliden-β-L-arabinopyranosid
• 英文别名: Benzyl-2-O-p-tosyl-3,4-O-isopropyliden-β-L-arabinopyranosid；(+)-benzyl-3,4-O-isopropyliden-2-O-(p-toluolsulfonyl)-β-L-arabinopyranoside；benzyl 3,4-O-isopropylidene-2-O-p-tosyl-β-L-arabinopyranoside；[(3aS,6S,7R,7aS)-2,2-dimethyl-6-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] 4-methylbenzenesulfonate
• CAS: 68753-33-3
• 化学式: C₂₂H₂₆O₇S
• 分子量: 434.51
• InChiKey: CRILAMFSBRBBIS-BURNTYAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzyl-2-O-p-toluolsulfonyl-3,4-O-isopropyliden-β-L-arabinopyranosid 在 吡啶 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 benzyl 2,3-anhydro-4-O-trifluoromethanesulfonyl-β-L-ribopyranoside
  参考文献：
  名称：

  Khan, Noshena; Al-Abed, Yousef; Kohlbau, Hans-Juergen, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1996, vol. 51, # 12, p. 1781 - 1790

  摘要：

  DOI：
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 盐酸 、 对甲苯磺酸 作用下， 反应 62.0h， 生成 Benzyl-2-O-p-toluolsulfonyl-3,4-O-isopropyliden-β-L-arabinopyranosid
  参考文献：
  名称：

  一种方法来手性η 4 -丁二烯-的Fe（CO）3个配合物通过的非外消旋2 -烷氧基-4-乙烯基-2,5-二氢呋喃衍生物的非对映选择性络合

  摘要：

  （+）- L-阿拉伯糖衍生的2-苄氧基-4-乙烯基-2,5-二氢呋喃衍生物（8）与Fe 2（CO）9在醚中的络合非对映选择性地提供相应的外-和内切-η 4 -二烯的Fe（CO）3个配合物9和10以约1:1的比例：3的络合产物的相对（绝对和）构型通过的分析方法的组合来确定（CD，NMR， X射线）。

  DOI：

  10.1016/s0040-4039(00)60723-2

文献信息

• Nucleoside Analogues with a 1,3-DieneFe(CO)₃Substructure: Stereoselective Synthesis, Configurational Assignment, and Apoptosis-Inducing Activity
  作者：Christoph Hirschhäuser、Juraj Velcicky、Daniel Schlawe、Erik Hessler、André Majdalani、Jörg-Martin Neudörfl、Aram Prokop、Thomas Wieder、Hans-Günther Schmalz

  DOI：10.1002/chem.201301672

  日期：2013.9.23

  The synthesis and stereochemical assignment of two classes of iron‐containing nucleoside analogues, both of which contain a butadieneFe(CO)3 substructure, is described. The first type of compounds are Fe(CO)3‐complexed 3′‐alkenyl‐2′,3′‐dideoxy‐2′,3′‐dehydro nucleosides (2,5‐dihydrofuran derivatives), from which the second class of compounds is derived by formal replacement of the ring oxygen atom

  描述了两类含丁二烯Fe（CO）3亚结构的含铁核苷类似物的合成和立体化学分配。第一类化合物是Fe（CO）3络合的3'-烯基-2'，3'-二脱氧-2'，3'-脱氢核苷（2,5-二氢呋喃衍生物），第二类化合物由CH 2正式取代环上的氧原子而得基团（碳环核苷类似物）。这些化合物是通过金属辅助引入核碱基以立体选择性的方式制备的。呋喃类中间体是由碳水化合物（如甲基-吡喃葡萄糖苷）制备的，而碳环化合物是通过分子内Pauson-Khand反应获得的。X射线结构分析证实了基于NMR和CD光谱的立体化学分配。生物学研究表明，某些复合物具有明显的凋亡诱导特性（通过不寻常的不依赖caspase 3的但依赖ROS的途径）。此外，还确定了一些构效关系，这也是设计和合成荧光素和生物素标记的结合物的前提。
• Efficient synthesis of 2-deoxy-l-erythro-pentose (2-deoxy-l-ribose) from l-arabinose
  作者：Youhoon Chong、Chung K Chu

  DOI：10.1016/s0008-6215(01)00329-9

  日期：2002.3

  2-deoxy-L-erythro-pentose (2-deoxy-L-ribose) starting from L-arabinose was developed using Barton-type free-radical deoxygenation reaction as a key step. The radical precursor, a phenoxythiocarbonyl ester, was prepared in situ, and the most efficient deoxygenation was achieved by slow addition of tributyltin hydride to the reaction mixture.

  以Barton型自由基脱氧反应为关键步骤，开发了一种从L-阿拉伯糖开始大规模合成2-deoxy-L-赤-戊糖（2-deoxy-L-核糖）的有效实用途径。 。原位制备自由基前体苯氧基硫代羰基酯，并通过向反应混合物中缓慢添加氢化三丁基锡来实现最有效的脱氧。
• Tschakert, Jochen; Voelter, Wolfgang, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 5, p. 702 - 716
  作者：Tschakert, Jochen、Voelter, Wolfgang

  DOI：——

  日期：——
• 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.