2-acetamido-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactopyranose | 318487-85-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactopyranose
• 英文别名: (2R,3R,4R,5S)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate；2-acetamido-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol；[(2R,3R,4R,5S)-5-acetamido-3,4-diacetyloxyoxan-2-yl]methyl acetate
• CAS: 318487-85-3
• 化学式: C₁₄H₂₁NO₈
• 分子量: 331.323
• InChiKey: CDFUEUPGVFCGDY-DGAVXFQQSA-N

物化性质

• 沸点：
  486.2±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactopyranose 在 盐酸 作用下， 以 水 为溶剂， 以68%的产率得到(2R,3R,4R,5S)-5-amino-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol hydrochloride
  参考文献：
  名称：

  [EN] IN VIVO ASSEMBLY OF ASGPR BINDING THERAPEUTICS
  [FR] ASSEMBLAGE IN VIVO D'AGENTS THÉRAPEUTIQUES DE LIAISON À ASGPR

  摘要：

  公开号：

  WO2022035997A9
• 作为产物：
  描述：

  苯基硒基-2-叠氮基-3,4,6-三-O-乙酰基-α-D-吡喃半乳糖苷 在 三乙基硼 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 2-acetamido-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactopyranose
  参考文献：
  名称：

  基于N-酰基半乳糖胺的自由基介导的α-C-糖苷合成。

  摘要：

  [结构] N-酰基2-氨基-2-脱氧半乳糖（酰基= MeCO，CF（3）CO，t-BuOCO）的C-糖苷可通过用活化的烯烃捕获异头基团以立体选择性方式获得。使用异头硒化物，在避免竞争性还原的条件下进行自由基的产生和捕获，并且该化学方法已用于合成O-苄基α-D-GalNAc的新型C-糖苷类似物。

  DOI：

  10.1021/ol006682c

文献信息

• Galacto, Gluco, Manno<i>,</i> and Disaccharide-Based <i>C-</i>Glycosides of 2-Amino-2-deoxy Sugars
  作者：Laura Grant、Yan Liu、Kenneth E. Walsh、Daryl S. Walter、Timothy Gallagher

  DOI：10.1021/ol0269695

  日期：2002.12.1

  underwent facile C-Se homolysis to provide the corresponding anomeric radicals, which were trapped with alkenes to give C-glycosides. This provides a general entry to alpha-C-glycosides based on 2-amino-2-deoxy sugars that is also applicable to disaccharide variants.

  [反应：见正文]从易得的前体开始，通过一或两个步骤的方法制备衍生自GalNAc，GlcNAc和ManNAc的硒代糖苷。对异头硒化物进行轻松的C-Se均质分解，以提供相应的异头自由基，这些自由基被烯烃捕获，得到C-糖苷。这提供了基于2-氨基-2-脱氧糖的α-C-糖苷的一般入口，其也适用于二糖变体。
• PEPTIDE CONTAINING CONJUGATES FOR DUAL MOLECULAR DELIVERY OF OLIGONUCLEOTIDES
  申请人：MERCK SHARP & DOHME CORP.

  公开号：EP3610884A1

  公开（公告）日：2020-02-19

  Disclosed herein is a peptide containing conjugate comprising (P)c-(L)d-(G)e, wherein: P is a peptide having Seq ID No. 1710; L is a linker and each occurance of L is independently selected from Table 3; G is a targeting ligand and each occurance of G is independently selected from Table 4; d is 0, 1, 2, 3, 4, 5 or 6; and each of c and e is independently 1, 2, 3, 4, 5 or 6. The conjugate can be administered to a subject either alone or in combination with a composition comprising R-(L)a-(G)b, wherein R is an oligonucleotide as defined herein, to inhibit expression of a gene of the subject.

  本文公开了一种包含(P)c-(L)d-(G)e的多肽共轭物，其中： P是具有Seq ID No.1710的多肽；L是连接体，且L的每个出现独立地选自表3；G是靶向配体，且G的每个出现独立地选自表4；d是0、1、2、3、4、5或6；以及c和e的每个出现独立地为1、2、3、4、5或6。该共轭物可单独或与包含 R-(L)a-(G)b（其中 R 是本文定义的寡核苷酸）的组合物结合施用给受试者，以抑制受试者基因的表达。
• Oligonucleotide-ligand conjugates and process for their preparation
  申请人：ALNYLAM PHARMACEUTICALS, INC.

  公开号：US10808246B2

  公开（公告）日：2020-10-20

  The present invention relates to ligand conjugates of iRNA agents (such as siRNA) of the formula

  本发明涉及式如下的 iRNA 制剂（如 siRNA）的配体共轭物
• Tetragalnac and peptide containing conjugates and methods for delivery of oligonucleotides
  申请人：Sirna Therapeutics, Inc.

  公开号：US11117917B2

  公开（公告）日：2021-09-14

  Disclosed herein is a modular composition comprising 1) an oligonucleotide; 2) one or more tetraGalNAc ligands of Formula (I), which may be the same or different; optionally, 3) one or more linkers, which may be the same or different; 4) one or more peptides independently selected from Table 3, which may be the same or different; and optionally, 5) one or more targeting ligands, solubilizing agents, pharmacokinetics enhancing agents, lipids, and/or masking agents.

  本文公开了一种模块化组合物，包括：1）寡核苷酸；2）一种或多种式（I）的四GalNAc配体，它们可以相同或不同；任选地，3）一种或多种连接体，它们可以相同或不同；4）一种或多种独立选自表3的肽，它们可以相同或不同；任选地，5）一种或多种靶向配体、增溶剂、药代动力学增强剂、脂质和/或掩蔽剂。
• Design, synthesis and evaluation of monovalent ligands for the asialoglycoprotein receptor (ASGP-R)
  作者：Daniela Stokmaier、Oleg Khorev、Brian Cutting、Rita Born、Daniel Ricklin、Thomas O.G. Ernst、Fabienne Böni、Kathrin Schwingruber、Martin Gentner、Matthias Wittwer、Morena Spreafico、Angelo Vedani、Said Rabbani、Oliver Schwardt、Beat Ernst

  DOI：10.1016/j.bmc.2009.08.049

  日期：2009.10

  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.