(2R,3R,4R,5S)-5-amino-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol | 1196658-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S)-5-amino-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
• 英文别名: 2-amino-1,5-anhydro-D-galactitol；Deoxygalactosamine；(2R,3R,4R,5S)-5-amino-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 1196658-66-8
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: MXRBVRXQDKNIBH-KCDKBNATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.9
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-5-amino-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol 在 copper(ll) sulfate pentahydrate 、 triflic azide 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 生成 1,5-anhydro-2-azido-2-deoxy-D-galactitol
  参考文献：
  名称：

  Design, synthesis and evaluation of monovalent ligands for the asialoglycoprotein receptor (ASGP-R)

  摘要：

  A series of novel aryl-substituted triazolyl D-galactosamine derivatives was synthesized as ligands for the carbohydrate recognition domain of the major subunit H1 (H1-CRD) of the human asialoglycoprotein receptor (ASGP-R). The compounds were biologically evaluated with a newly developed competitive binding assay, surface plasmon resonance and by a competitive NMR binding experiment. With compound 1b, a new ligand with a twofold improved affinity to the best so far known D-GalNAc was identified. This small, drug-like ligand can be used as targeting device for drug delivery to hepatocytes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.049
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactopyranose 在 18-冠醚-6 、 水 、 potassium hydroxide 作用下， 反应 6.5h， 生成 (2R,3R,4R,5S)-5-amino-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
  参考文献：
  名称：

  Design, synthesis and evaluation of monovalent ligands for the asialoglycoprotein receptor (ASGP-R)

  摘要：

  A series of novel aryl-substituted triazolyl D-galactosamine derivatives was synthesized as ligands for the carbohydrate recognition domain of the major subunit H1 (H1-CRD) of the human asialoglycoprotein receptor (ASGP-R). The compounds were biologically evaluated with a newly developed competitive binding assay, surface plasmon resonance and by a competitive NMR binding experiment. With compound 1b, a new ligand with a twofold improved affinity to the best so far known D-GalNAc was identified. This small, drug-like ligand can be used as targeting device for drug delivery to hepatocytes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.049

文献信息

• [EN] ASGPR-BINDING COMPOUNDS FOR THE DEGRADATION OF EXTRACELLULAR PROTEINS<br/>[FR] COMPOSÉS SE LIANT À L'ASGPR POUR LA DÉGRADATION DE PROTÉINES EXTRACELLULAIRES
  申请人：AVILAR THERAPEUTICS INC

  公开号：WO2021155317A1

  公开（公告）日：2021-08-05

  Compounds and compositions that have an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein are described.

  描述了将一个与外细胞蛋白结合配体结合的阿斯利康糖蛋白受体（ASGPR）结合配体的化合物和组合物，用于选择性降解体内靶外细胞蛋白以治疗由外细胞蛋白介导的疾病。
• [EN] IN VIVO ASSEMBLY OF ASGPR BINDING THERAPEUTICS<br/>[FR] ASSEMBLAGE IN VIVO D'AGENTS THÉRAPEUTIQUES DE LIAISON À ASGPR
  申请人：AVILAR THERAPEUTICS INC

  公开号：WO2022035997A9

  公开（公告）日：2022-03-17
• TETRAGALNAC AND PEPTIDE CONTAINING CONJUGATES AND METHODS FOR DELIVERY OF OLIGONUCLEOTIDES
  申请人：Sirna Therapeutics, Inc.

  公开号：EP2844662B1

  公开（公告）日：2020-09-16
• PEPTIDE CONTAINING CONJUGATES FOR DUAL MOLECULAR DELIVERY OF OLIGONUCLEOTIDES
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3065758B1

  公开（公告）日：2019-09-25
• ASGPR-BINDING COMPOUNDS FOR THE DEGRADATION OF EXTRACELLULAR PROTEINS
  申请人：Avila Therapeutics, Inc.

  公开号：EP4097138A1

  公开（公告）日：2022-12-07