2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)valinyl)amino-1,3,4,6-tetra-O-benzyl-2-deoxy-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)valinyl)amino-1,3,4,6-tetra-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: (2S)-2-[2-(5,5-dimethyl-1,3-dioxan-2-yl)ethylamino]-3-methyl-N-[(2S,3R,4R,5S,6R)-2,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]butanamide
• 化学式: C₄₇H₆₀N₂O₈
• 分子量: 781.002
• InChiKey: WZNWAPHFFZMFIA-NZTUAYMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,1,3,3-四甲氧基丙烷 在 盐酸 、 sodium cyanoborohydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 2.25h， 生成 2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)valinyl)amino-1,3,4,6-tetra-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Design, synthesis and evaluation of a novel class of glucosamine mimetic peptides containing 1,3-dioxane

  摘要：

  A number of novel 2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)aminoacyl)amino-2-deoxy-D-glucopyranoside were synthesized from a readily available starting material, glucosamine, 2,2-dimethyl-1,3-propanediol and 1,1,3,3-tetramethoxypropane, and evaluated for their anti-inflammatory activity. Our results showed that all of the compounds tested exhibited a significant inhibition of xylene-induced inflammation in mice. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.062

文献信息

• Design, synthesis and evaluation of a novel class of glucosamine mimetic peptides containing 1,3-dioxane
  作者：Li Zeng、Guichao Xu、Pengchao Gao、Meng Zhang、Hong Li、Jianwei Zhang

  DOI：10.1016/j.ejmech.2015.01.062

  日期：2015.3

  A number of novel 2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)aminoacyl)amino-2-deoxy-D-glucopyranoside were synthesized from a readily available starting material, glucosamine, 2,2-dimethyl-1,3-propanediol and 1,1,3,3-tetramethoxypropane, and evaluated for their anti-inflammatory activity. Our results showed that all of the compounds tested exhibited a significant inhibition of xylene-induced inflammation in mice. (C) 2015 Elsevier Masson SAS. All rights reserved.