ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-1-thio-α-D-mannopyranoside | 189105-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-1-thio-α-D-mannopyranoside
• 英文别名: [(1S,3R,4R,6R,7S,8S,10S)-6-ethylsulfanyl-1,10-dimethoxy-7-phenylmethoxy-2,5,9-trioxatricyclo[8.4.0.03,8]tetradecan-4-yl]methanol
• CAS: 189105-30-4
• 化学式: C₂₃H₃₄O₇S
• 分子量: 454.585
• InChiKey: ATSDRZYFGIDHBP-NUNPFQGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-1-thio-α-D-mannopyranoside 在 氢氧化钾 、 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Mannose-Based Peptidomimetics Selectively Blocking Integrin α4β7 Binding to Mucosal Addressin Cell Adhesion Molecule-1

  摘要：

  As part of our ongoing research in the development of alpha4beta7 integrin antagonists, we are interested in peptidomimetics based on a rigid scaffold to allow the display of essential side chains in a suitable binding conformation while eliminating backbone amide bonds and therefore improving pharmacokinetic parameters of the drug. Except for a few examples, peptidomimetics scaffolds have only been moderately successful and often yield molecules that lack the potency of their peptide counterparts. However, we present herein a successful application of using a rigid scaffold. Starting from a mannopyranoside analogue previously discovered in our laboratory as an inhibitor of the alpha4beta1/vascular cell adhesion molecule interaction, a biased library of functionalized carbohydrates was developed. One compound emerged from this library as an active and selective antagonist toward the alpha4beta7/mucosal addressin cell adhesion molecule interaction. Conformational. implications and the relevance of different pharmacophoric patterns will be discussed in order to explain the reverse selectivity and enhanced affinity.

  DOI：

  10.1021/jm020487h
• 作为产物：
  描述：

  1,1,2,2-四甲氧基环己烷 在 camphor-10-sulfonic acid 、 sodium hydride 、 原甲酸三甲酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Grice, Peter; Ley, Steven V.; Pietruszka, Joerg, Journal of the Chemical Society. Perkin transactions I, 1997, # 4, p. 351 - 363

  摘要：

  DOI：

文献信息

• Chemoselective<i>O</i>-Benzylation of the Propargylic Hydroxy Group in Polyols
  作者：Ji Ho Lee、Chang Ho Oh

  DOI：10.1002/ejoc.201201086

  日期：2012.10

  the highly chemoselective benzylation of propargylic hydroxy groups in the presence of other hydroxy groups under very usual conditions involving benzyl bromide and sodium hydroxide in DMF at room temperature. This methodology has a high synthetic utility for the selective protection of hydroxy groups at the propargylic position among various other hydroxy groups in complex molecules.

  我们已经发现在非常常见的条件下炔丙基羟基在其他羟基存在下的高度化学选择性苄基化，包括苄基溴和氢氧化钠在室温下在 DMF 中。该方法对于复杂分子中各种其他羟基中炔丙基位置的羟基的选择性保护具有很高的合成效用。
• Grice, Peter; Ley, Steven V.; Pietruszka, Joerg, Journal of the Chemical Society. Perkin transactions I, 1997, # 4, p. 351 - 363
  作者：Grice, Peter、Ley, Steven V.、Pietruszka, Joerg、Priepke, Henning W. M.、Warriner, Stuart L.

  DOI：——

  日期：——
• Synthesis and Structure−Activity Relationship of Mannose-Based Peptidomimetics Selectively Blocking Integrin α4β7 Binding to Mucosal Addressin Cell Adhesion Molecule-1
  作者：Elsa Locardi、Jürgen Boer、Armin Modlinger、Anja Schuster、Bernhard Holzmann、Horst Kessler

  DOI：10.1021/jm020487h

  日期：2003.12.1

  As part of our ongoing research in the development of alpha4beta7 integrin antagonists, we are interested in peptidomimetics based on a rigid scaffold to allow the display of essential side chains in a suitable binding conformation while eliminating backbone amide bonds and therefore improving pharmacokinetic parameters of the drug. Except for a few examples, peptidomimetics scaffolds have only been moderately successful and often yield molecules that lack the potency of their peptide counterparts. However, we present herein a successful application of using a rigid scaffold. Starting from a mannopyranoside analogue previously discovered in our laboratory as an inhibitor of the alpha4beta1/vascular cell adhesion molecule interaction, a biased library of functionalized carbohydrates was developed. One compound emerged from this library as an active and selective antagonist toward the alpha4beta7/mucosal addressin cell adhesion molecule interaction. Conformational. implications and the relevance of different pharmacophoric patterns will be discussed in order to explain the reverse selectivity and enhanced affinity.
• Design, Synthesis, and Biological Evaluation ofα4β1 Integrin Antagonists Based onβ-D-Mannose as Rigid Scaffold
  作者：Jürgen Boer、Dirk Gottschling、Anja Schuster、Bernhard Holzmann、Horst Kessler

  DOI：10.1002/1521-3773(20011015)40:20<3870::aid-anie3870>3.0.co;2-x

  日期：2001.10.15

  A cyclic peptide role model was used for the design and synthesis of a new class of biologically active and α4 -selective integrin antagonists (e.g. 1) based on β-D-mannose. These carbohydrate-based peptidomimetics were synthesized to include the functional groups of their cyclic peptide precursors without the redundant amide backbone.