ethyl-2-O-benzyl-6-O-isobutyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside | 400835-49-6

• 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-6-O-isobutyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-ethylsulfanyl-4,5-dimethoxy-6-(2-methylpropoxymethyl)-3-phenylmethoxyoxane
• CAS: 400835-49-6
• 化学式: C₂₁H₃₄O₅S
• 分子量: 398.564
• InChiKey: RDJWFHXZPUTVPG-CRSSMBPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl-2-O-benzyl-6-O-isobutyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 以91%的产率得到(3S,4S,5R,6R)-3-Benzyloxy-6-isobutoxymethyl-4,5-dimethoxy-tetrahydro-pyran-2-ol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation ofα4β1 Integrin Antagonists Based onβ-D-Mannose as Rigid Scaffold

  摘要：

  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.

  DOI：

  10.1002/1521-3773(20011015)40:20<3870::aid-anie3870>3.0.co;2-x
• 作为产物：
  描述：

  (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isobutoxymethyl-tetrahydro-pyran-3,4-diol 、 碘甲烷 在 双(三甲基硅烷基)氨基钾 作用下， 以87%的产率得到ethyl-2-O-benzyl-6-O-isobutyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation ofα4β1 Integrin Antagonists Based onβ-D-Mannose as Rigid Scaffold

  摘要：

  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.

  DOI：

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

文献信息

• 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.