(2S)-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropionic acid | 1449303-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropionic acid
• CAS: 1449303-89-2
• 化学式: C₃₈H₄₂O₈
• 分子量: 626.747
• InChiKey: ALLLOWYUKYCGCK-SFGDPAIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  46.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S)-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropionic acid 、 盐酸金刚烷胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 1-羟基苯并三唑 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以66%的产率得到(2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide
  参考文献：
  名称：

  Experimental and computational study of the complexation of adamantyl glycosides with β-cyclodextrin

  摘要：

  Complexation of alpha- and beta-anomers of adamantyl galactosides and adamantyl mannosides, having different configuration of the chiral linker connecting the sugar and the adamantamine (AMA) subunits, with beta-cyclodextrin (beta-CD) was investigated by means of NMR spectroscopy, microcalorimetric titrations and computational studies. The synthesis of adamantyl galactosides is also reported.The experimental investigations are consistent with the formation of 1:1 complexes in which the hydrophilic part of the guest protruded out of the secondary rim. The beta-cyclodextrin was shown to be a rather efficient binder for the examined guests in water, primarily as a consequence of the enthalpically favourable inclusion of the adamantyl moiety within the hydrophobic cavity of the host.The structures of AMA derivatives complexes were modelled by combination of molecular and quantum mechanics - B3LYP/6-31G(d) in implicitly modelled water (PCM). The differences in the stability of primary and secondary complexes were observed. The main reasons for that could be more pronounced dehydration of the hydrophilic part of the guest upon complete adamantane inclusion in the complexes of primary type and the different hydrogen bonding pattern at the primary and secondary CD rims. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.097
• 作为产物：
  描述：

  在 三氟化硼乙醚 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 26.75h， 生成 (2S)-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropionic acid
  参考文献：
  名称：

  Experimental and computational study of the complexation of adamantyl glycosides with β-cyclodextrin

  摘要：

  Complexation of alpha- and beta-anomers of adamantyl galactosides and adamantyl mannosides, having different configuration of the chiral linker connecting the sugar and the adamantamine (AMA) subunits, with beta-cyclodextrin (beta-CD) was investigated by means of NMR spectroscopy, microcalorimetric titrations and computational studies. The synthesis of adamantyl galactosides is also reported.The experimental investigations are consistent with the formation of 1:1 complexes in which the hydrophilic part of the guest protruded out of the secondary rim. The beta-cyclodextrin was shown to be a rather efficient binder for the examined guests in water, primarily as a consequence of the enthalpically favourable inclusion of the adamantyl moiety within the hydrophobic cavity of the host.The structures of AMA derivatives complexes were modelled by combination of molecular and quantum mechanics - B3LYP/6-31G(d) in implicitly modelled water (PCM). The differences in the stability of primary and secondary complexes were observed. The main reasons for that could be more pronounced dehydration of the hydrophilic part of the guest upon complete adamantane inclusion in the complexes of primary type and the different hydrogen bonding pattern at the primary and secondary CD rims. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.097