1,5-anhydro-6-azido-6-deoxy-D-glucitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-6-azido-6-deoxy-D-glucitol
• 英文别名: (2R,3S,4R,5S)-2-(azidomethyl)oxane-3,4,5-triol
• 化学式: C₆H₁₁N₃O₄
• 分子量: 189.171
• InChiKey: MEGCBJOTGBEPOC-SLPGGIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-6-azido-6-deoxy-D-glucitol 在 氢气 、 palladium(II) hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Dansyl C-葡糖苷作为抗内毒素休克的新型药物

  摘要：

  丹斯尔跟我来！从甲基α- D-吡喃葡萄糖苷合成了一个小的萘基葡萄糖衍生物文库，没有进行保护/脱保护步骤。一个文库成员Dansyl C- glucoside 5表现出非凡的抗炎活性，以25μgkg -1的剂量保护100％的小鼠免于败血症。

  DOI：

  10.1002/cmdc.201000282
• 作为产物：
  描述：

  2,3,4-Tri-O-acetyl-1,5-anhydro-6-O-tolyl-p-sulfonyl-D-glucitol 在 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1,5-anhydro-6-azido-6-deoxy-D-glucitol
  参考文献：
  名称：

  Strong competitive inhibition of porcine pancreaticalpha-amylase by aminodeoxy derivatives of maltose and maltotriose

  摘要：

  The syntheses are described of 6-amino-6-deoxymaltose (2), the 6-amino-6-deoxy (4), 6'-amino-6'-deoxy (6), and 6''-amino-6''-deoxy (8) derivatives of maltotriose, and the methyl alpha- (10) and beta-glycoside (12) and the 1-deoxy derivative (16) of 4. The K(i) values (muM) of these competitive inhibitors of porcine pancreatic alpha-amylase were: 2, 88; 4, 1.9; 6, 2.0; 8, 175; 10, 360; 12, 9000; 16, 7600 (cf. 1800 for maltotriose and 3000 for methyl alpha-maltotrioside). The low values for 4 and 6 reflect reinforcement of the normal binding by ionic attraction and possibly, interaction of the reducing end groups with the protein.

  DOI：

  10.1016/s0008-6215(92)84241-j

文献信息

• [EN] LIGAND CONJUGATES FOR DELIVERY OF THERAPEUTICALLY ACTIVE AGENTS<br/>[FR] CONJUGUÉS DE LIGANDS POUR L'ADMINISTRATION D'AGENTS THÉRAPEUTIQUEMENT ACTIFS
  申请人：[en]HEPAGENE THERAPEUTICS (HK) LIMITED

  公开号：WO2023011597A1

  公开（公告）日：2023-02-09

  Provided are compounds of Formula (I) as novel ligand conjugates, and use thereof for delivering therapeutically active agents. The compounds have the advantages for in vitro and/or in vivo delivery of therapeutically active agents, e.g., iRNA agents.
• Dansyl C-Glucoside as a Novel Agent Against Endotoxic Shock
  作者：Barbara La Ferla、Valerio Spinosa、Giuseppe D'Orazio、Marco Palazzo、Andrea Balsari、Anastasia A. Foppoli、Cristiano Rumio、Francesco Nicotra

  DOI：10.1002/cmdc.201000282

  日期：——

  Come dansyl with me! A small library of naphthyl gluco derivatives was synthesised from methyl α‐D‐glucopyranoside without protection/deprotection steps. One library member, dansyl C‐glucoside 5, showed an extraordinary anti‐inflammatory activity, protecting 100 % of mice from sepsis at a dose of 25 μg kg−1.

  丹斯尔跟我来！从甲基α- D-吡喃葡萄糖苷合成了一个小的萘基葡萄糖衍生物文库，没有进行保护/脱保护步骤。一个文库成员Dansyl C- glucoside 5表现出非凡的抗炎活性，以25μgkg -1的剂量保护100％的小鼠免于败血症。
• Strong competitive inhibition of porcine pancreaticalpha-amylase by aminodeoxy derivatives of maltose and maltotriose
  作者：Jochen Lehmann、Markus Schmidt-Schuchardt、Jürgen Steck

  DOI：10.1016/s0008-6215(92)84241-j

  日期：1992.12

  The syntheses are described of 6-amino-6-deoxymaltose (2), the 6-amino-6-deoxy (4), 6'-amino-6'-deoxy (6), and 6''-amino-6''-deoxy (8) derivatives of maltotriose, and the methyl alpha- (10) and beta-glycoside (12) and the 1-deoxy derivative (16) of 4. The K(i) values (muM) of these competitive inhibitors of porcine pancreatic alpha-amylase were: 2, 88; 4, 1.9; 6, 2.0; 8, 175; 10, 360; 12, 9000; 16, 7600 (cf. 1800 for maltotriose and 3000 for methyl alpha-maltotrioside). The low values for 4 and 6 reflect reinforcement of the normal binding by ionic attraction and possibly, interaction of the reducing end groups with the protein.