methyl 2-amino-2-deoxy-4,6-isopropylidene-3-O-tetradecanoyl-α-D-glucopyranoside | 470665-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-amino-2-deoxy-4,6-isopropylidene-3-O-tetradecanoyl-α-D-glucopyranoside
• CAS: 470665-49-7
• 化学式: C₂₄H₄₅NO₆
• 分子量: 443.624
• InChiKey: WQTSMAKAOQDDAY-KNQBKSORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  89.24
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-amino-2-deoxy-4,6-isopropylidene-3-O-tetradecanoyl-α-D-glucopyranoside 在 sodium azide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 水 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  SYNTHESIS OF PSEUDO-DISACCHARIDE ANALOGUES OF LIPID A: HAPTENS FOR THE GENERATION OF ANTIBODIES WITH GLYCOSIDASE ACTIVITY TOWARDS LIPID A

  摘要：

  In order to develop a generic treatment of sepsis caused by infections with Gram-negative bacteria, a series of pseudo-disaccharide analogues of lipid A (1-5) was synthesized. These adducts not only harbor a 2-acylaminodideoxynojirimycin unit mimicking the transition state of the,glycosidic hydrolysis, but also a 2-N, 3-O-diacylated glucosamine moiety capable of generating catalytic antibodies with more selective glycosidase properties towards lipid A.

  DOI：

  10.1081/car-120004331
• 作为产物：
  描述：

  ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 100.0h， 生成 methyl 2-amino-2-deoxy-4,6-isopropylidene-3-O-tetradecanoyl-α-D-glucopyranoside
  参考文献：
  名称：

  SYNTHESIS OF PSEUDO-DISACCHARIDE ANALOGUES OF LIPID A: HAPTENS FOR THE GENERATION OF ANTIBODIES WITH GLYCOSIDASE ACTIVITY TOWARDS LIPID A

  摘要：

  In order to develop a generic treatment of sepsis caused by infections with Gram-negative bacteria, a series of pseudo-disaccharide analogues of lipid A (1-5) was synthesized. These adducts not only harbor a 2-acylaminodideoxynojirimycin unit mimicking the transition state of the,glycosidic hydrolysis, but also a 2-N, 3-O-diacylated glucosamine moiety capable of generating catalytic antibodies with more selective glycosidase properties towards lipid A.

  DOI：

  10.1081/car-120004331