(2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isopropoxymethyl-tetrahydro-pyran-3,4-diol | 647030-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isopropoxymethyl-tetrahydro-pyran-3,4-diol
• CAS: 647030-03-3
• 化学式: C₁₈H₂₈O₅S
• 分子量: 356.483
• InChiKey: NHSRWHPHYSQCNC-DFBDCSAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isopropoxymethyl-tetrahydro-pyran-3,4-diol 、 碘甲烷 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以70%的产率得到ethyl-2-O-benzyl-6-O-isopropyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside
  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：

  ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isopropyl-1-thio-α-D-mannopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到(2R,3S,4S,5S,6R)-5-Benzyloxy-6-ethylsulfanyl-2-isopropoxymethyl-tetrahydro-pyran-3,4-diol
  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