2-phenylethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside | 74590-54-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-phenylethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
• 英文别名: 2-phenylethyl 2,3,4,6-tetra-O-acetyl-1-thio-alpha-d-mannopyranoside；[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(2-phenylethylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 74590-54-8
• 化学式: C₂₂H₂₈O₉S
• 分子量: 468.525
• InChiKey: NQDDJQKMPBUCKZ-LXHROKJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-phenylethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 在 甲醇 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 (R(S))-2-phenylethyl α-d-mannopyranosyl sulfoxide
  参考文献：
  名称：

  α-d-Mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II

  摘要：

  Human Golgi alpha-mannosidase II (hGM) is a pharmaceutical target for the design of inhibitors with antitumor activity. Nanomolar inhibitors of hGM exhibit unwanted co-inhibition of the human lysosomal alpha-mannosidase (hLM). Hence, improving specificity of the inhibitors directed toward hGM is desired in order to use them in cancer chemotherapy. We report on the rapid synthesis of D-mannose derivatives having one of the RS-. R(SO)- or R(SO(2))- groups at the alpha-anomeric position. Inhibitory properties of thirteen synthesized alpha-D-mannopyranosides were tested against the recombinant enzyme Drosophila melanogaster homolog of hGM (dGMIIb) and hLM (dLM408). Derivatives with the sulfonyl [R(SO(2))-] group exhibited inhibitory activities at the mM level toward both dGMIIb (IC(50) = 1.5-2.5 mM) and dLM408 (IC(50) = 1.0-2.0 mM). Among synthesized, only the benzylsulfonyl derivative showed selectivity toward dGMIIb. Its inhibitory activity was explained based on structural analysis of the built 3-D complexes of the enzyme with the docked compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.012
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 potassium disulphite 、 potassium carbonate 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 2-phenylethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  胰岛素样和胰岛素拮抗的碳水化合物衍生物。芳基和芳烷基D-甘露糖吡喃糖苷和1-硫代-D-甘露糖吡喃糖苷的合成。

  摘要：

  合成了许多新颖的芳基和芳烷基D-甘露糖吡喃糖苷和1-硫代-D-甘露糖吡喃糖苷，用于评估胰岛素样和胰岛素拮抗性质。通过Helferich和Schmitz-Hillebrecht的通用方法制备取代的苯基α-D-甘露糖吡喃糖苷，通过对应于芳族糖苷的迈克尔合成的方法制备取代的苯基1-硫代α-D-甘露糖吡喃糖苷，以及芳烷基。通过2,3,4,6-四-O-乙酰基-1-硫代-α-D-甘露吡喃糖的芳烷基化作用制备1-硫代-α-D-甘露吡喃糖苷（15），然后进行O-脱乙酰化。通过将2-O-乙酰基-α-D反应的产物2-S-（四-O-乙酰基-α-D-甘露吡喃糖基）-2-thiopseudourea氢溴酸盐中的mid基进行碱性裂解，得到化合物15。 -甘露糖基溴与硫脲。苄基1-硫代-β-D-甘露吡喃糖苷

  DOI：

  10.1016/s0008-6215(00)85657-8

文献信息

• Application of oxone immobilized on montmorillonite for an efficient oxidation of mannose thioglycoside
  作者：Monika Poláková、Ľuboš Jankovič、Lenka Kucková、Jozef Kožíšek

  DOI：10.1007/s00706-013-0964-0

  日期：2013.7

  A new solid system based on montmorillonite supported oxone has been developed and used for the oxidation of thiomannoside. The oxidation properties of oxone immobilized on montmorillonite were affected by polarity of the solvent, resulting in the different sulfoxide to sulfone ratios as the products. Toluene was the only solvent favouring sulfone formation over sulfoxide. X-ray crystal structures of the starting compound as well as the corresponding sulfoxide (major epimer Rs) and sulfone are also reported.