1-(β-D-mannopyranosyl)propane | 141042-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-mannopyranosyl)propane
• 英文别名: 1-deoxy-1-propyl-β-D-mannopyranose；(2R,3S,4R,5S,6S)-2-(hydroxymethyl)-6-propyloxane-3,4,5-triol
• CAS: 141042-25-3
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: PNQDGCOQVLHKHH-XDQCBXAXSA-N

物化性质

• 沸点：
  383.1±42.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene 在 palladium on activated charcoal 、 cyclooctadiene-bis(methyldiphenylphosphine)-iridium hexafluorophosphate 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 54.0h， 生成 1-(β-D-mannopyranosyl)propane
  参考文献：
  名称：

  Subtle Stereochemical and Electronic Effects in Iridium-Catalyzed Isomerization of C-Allyl Glycosides

  摘要：

  Stereoselective isomerization of C-allyl glycosides into (E)-C-vinyl glycosides or (Z)-exo-glycals was carried out in the presence of the cationic iridium(I) catalyst [(Ph2MeP)(2)Ir(cod)PF6]. The products of the isomerization were affected by the relative 1,2-stereochemical relationships and by the nature of the protecting groups. These effects are discussed along with a plausible reaction mechanism.

  DOI：

  10.1021/ol060671n

文献信息

• C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism
  作者：Carolyn Bertozzi、Mark Bednarski

  DOI：10.1016/0008-6215(92)80021-r

  日期：1992.1

  A series of C-mannopyranosyl derivatives have been synthesized and their inhibitory activity towards the receptor-mediated adhesion of E. coli to yeast cells has been tested. Total inhibition of yeast-cell agglutination by C-glycosyl derivatives 4 and 9 is achieved at a concentration approximately one order of magnitude lower than that of methyl alpha-D-mannopyranoside, indicating that the binding affinity to the receptor is related to the hydrophobicity of the carbon-linked side chain. A biotin-linked C-glycosyl derivative of mannose (compound 9) has been synthesized and used to target avidin and streptavidin to the bacterial cell surface. Of the C-glycosyl derivatives tested in our study, the conjugate of compound 9 with avidin had the highest avidity for the bacterial receptors, inhibiting agglutination at a concentration three orders of magnitude lower than methyl alpha-D-mannopyranoside. The use of such bifunctional compounds as the mannose-biotin conjugate 9 is a general strategy to target molecules to pathogenic organisms via their cell-surface carbohydrate receptors and to change the antigenicity of the bacterial cell surface.