benzyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 648417-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-3-[(2R,3R,4S,5R,6R)-5-azido-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[(2R,3R,4S,5R,6R)-4,5,6-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxane
• CAS: 648417-39-4
• 化学式: C₈₁H₈₅N₃O₁₄
• 分子量: 1324.58
• InChiKey: GWSLKONQOWHDCG-GQKFSIQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  98
• 可旋转键数：
  34
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  丁炔二醇 、 benzyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 以 氯苯 为溶剂， 反应 24.0h， 以70%的产率得到
  参考文献：
  名称：

  1,2,3-Triazoles and related glycoconjugates as new glycosidase inhibitors

  摘要：

  A series of saccharidyl-triazoles structurally related to acarbose were prepared and tested as inhibitors of glycosidases. They share in common a 1,4,5trisubstituted 1,2,3-triazole heterocycle as a functional element able to interact with the active site of the target enzymes. First, it was established that the heterocyclic core exhibits a moderate but highly selective a-glucosidase inhibitory activity. Then, it was confirmed that the inhibitory properties could be modulated by conjugation from one to five carbohydrate residues. The present study includes the regio- and stereocontrolled synthesis of novel non-fused 1,2,3-triazolo-pseudooligosaccharides as well as their evaluation as new glycosidase inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.033
• 作为产物：
  描述：

  benzyl 2,3-di-O-benzyl-4-O-methanesulfonyl-α-D-fucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium azide 、 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以95%的产率得到benzyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  阿卡波糖寡糖结构域的新合成。

  摘要：

  对阿卡波糖的寡糖结构域的合成进行了重新研究，并使用已经带有α-D-Glc-（1-4）-D-Glc键的麦芽糖受体和新的D-呋喃核糖基供体进行了优化。关键的糖基化步骤通过改变三个不同的参数得到了改善，特别是着眼于岩藻糖基残基，溶剂和促进剂的C-4保护基团。为了为设计新的阿卡波糖类似物打开进一步的衍生前景，将所得的三糖进一步转化为亲电子物质。用叠氮化物和硫氰酸根阴离子有效地进行了取代反应。还合成了另外两种可能有趣的三糖化合物，即C-4III胺和相应的异硫氰酸酯。

  DOI：

  10.1016/j.carres.2003.09.004

文献信息

• 1,2,3-Triazoles and related glycoconjugates as new glycosidase inhibitors
  作者：Régis Périon、Vincent Ferrières、M. Isabel García-Moreno、Carmen Ortiz Mellet、Raphaël Duval、José M. García Fernández、Daniel Plusquellec

  DOI：10.1016/j.tet.2005.07.033

  日期：2005.9

  A series of saccharidyl-triazoles structurally related to acarbose were prepared and tested as inhibitors of glycosidases. They share in common a 1,4,5trisubstituted 1,2,3-triazole heterocycle as a functional element able to interact with the active site of the target enzymes. First, it was established that the heterocyclic core exhibits a moderate but highly selective a-glucosidase inhibitory activity. Then, it was confirmed that the inhibitory properties could be modulated by conjugation from one to five carbohydrate residues. The present study includes the regio- and stereocontrolled synthesis of novel non-fused 1,2,3-triazolo-pseudooligosaccharides as well as their evaluation as new glycosidase inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.
• A new synthesis of the oligosaccharide domain of acarbose
  作者：Régis Périon、Lénaı̈ck Lemée、Vincent Ferrières、Raphaël Duval、Daniel Plusquellec

  DOI：10.1016/j.carres.2003.09.004

  日期：2003.11

  Synthesis of the oligosaccharide domain of acarbose was reinvestigated and was optimally performed using a maltosidic acceptor, already bearing a alpha-D-Glc-(1-->4)-D-Glc bond, and a new D-fucopyranosyl donor. The crucial glycosylation step was improved by varying three different parameters and notably by focusing on the C-4 protecting group of the fucosyl residue, solvent and promoter. The resulting

  对阿卡波糖的寡糖结构域的合成进行了重新研究，并使用已经带有α-D-Glc-（1-4）-D-Glc键的麦芽糖受体和新的D-呋喃核糖基供体进行了优化。关键的糖基化步骤通过改变三个不同的参数得到了改善，特别是着眼于岩藻糖基残基，溶剂和促进剂的C-4保护基团。为了为设计新的阿卡波糖类似物打开进一步的衍生前景，将所得的三糖进一步转化为亲电子物质。用叠氮化物和硫氰酸根阴离子有效地进行了取代反应。还合成了另外两种可能有趣的三糖化合物，即C-4III胺和相应的异硫氰酸酯。