3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(methylsulfonyl)propanol | 140909-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(methylsulfonyl)propanol
• 英文别名: 3-[(2R,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propyl methanesulfonate
• CAS: 140909-66-6
• 化学式: C₃₈H₄₄O₈S
• 分子量: 660.829
• InChiKey: LSBLDBMTSXHYKO-OHTWKVNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  47.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(methylsulfonyl)propanol 在 palladium dihydroxide 盐酸 、 氢气 、 叠氮化四丁基铵 作用下， 以 乙腈 为溶剂， 反应 29.0h， 生成 1-amino-3-(α-D-mannopyranosyl)propane hydrochloride
  参考文献：
  名称：

  C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism

  摘要：

  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.

  DOI：

  10.1016/0008-6215(92)80021-r
• 作为产物：
  描述：

  3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene 在 吡啶 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(methylsulfonyl)propanol
  参考文献：
  名称：

  2-苯基喹啉-糖杂化物作为可光转换的α-葡萄糖苷酶抑制剂

  摘要：

  合成了专门设计的2-苯基喹啉（PQ）-糖杂种1和2，并评估了它们对α-葡萄糖苷酶靶标的光降解活性。结果表明，在中性和水性条件下，在没有任何添加剂的情况下，用长波长紫外线照射后，PQ-甘露糖杂种2可以选择性且有效地光降解α-葡萄糖苷酶，并显着抑制其酶活性。此外，即使在复杂的细胞裂解物中，2也只有通过光照射才能选择性而有效地抑制α-葡萄糖苷酶的活性。

  DOI：

  10.1002/asia.201900203