ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside | 174314-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside
• CAS: 174314-06-8
• 化学式: C₁₇H₂₄Cl₃NO₉S
• 分子量: 524.804
• InChiKey: CRCQOHLIHKILST-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  126.46
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4-(benzyloxycarbonylamino)-N-{tris[13-hydroxy-2,6,10-trioxatridecyl]methyl}butyramide 、 ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以91%的产率得到N-(tris{13-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyloxy]-2,6,10-trioxatridecyl}methyl)-4-(benzyloxycarbonylamino)butyramide
  参考文献：
  名称：

  Trivalent, Gal/GalNAc-containing ligands designed for the asialoglycoprotein receptor

  摘要：

  A series of novel, fluorescent ligands designed to bind with high affinity and specificity to the asialoglycoprotein receptor (ASGP-R) has been synthesized and tested on human liver cells. The compounds bear three non-reducing, beta-linked Gal or GalNAc moieties linked to flexible spacers for an optimal spatial interaction with the binding site of the ASGP-R. The final constructs were selectively endocytosed by HepG2 cells derived from parenchymal liver cells-the major human liver cell type-in a process that was visualized with the aid of fluorescence microscopy. Furthermore, the internalization was analyzed with flow cytometry, which showed the process to be receptor-mediated and selective. The compounds described in this work could serve as valuable tools for studying hepatic endocytosis, and are suited as carriers for site-specific drug delivery to the liver. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.017
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-galactopyranose hydrochloride 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.42h， 生成 ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside
  参考文献：
  名称：

  N-Troc保护的糖基供体的糖基化。

  摘要：

  将N-Troc保护的（Troc = 2,2,2-三氯乙氧基羰基）葡萄糖胺和半乳糖胺糖基供体（1-O-乙酰基糖，溴糖和硫代糖苷）与相应的N-Phth保护的衍生物的糖基化为2 -（三甲基甲硅烷基）乙醇，2-溴乙醇，3-巯基丙酸甲酯，N-Fmoc保护的丝氨酸和2-（三甲基甲硅烷基）乙基6-O-苄基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖苷。N-Troc保护的供体比N-Phth保护的供体以更高的收率得到纯的β-糖苷。N-Troc保护基可通过用锌还原来去除，从而允许在同时包含N-Troc和N-Phth基团的寡糖中进行选择性N-脱保护。

  DOI：

  10.1016/0008-6215(95)00318-5

文献信息

• Synthetic, Structural, and Biosynthetic Studies of an Unusual Phospho-Glycopeptide Derived from α-Dystroglycan
  作者：Kai-For Mo、Tao Fang、Stephanie H. Stalnaker、Pamela S. Kirby、Mian Liu、Lance Wells、Michael Pierce、David H. Live、Geert-Jan Boons

  DOI：10.1021/ja205473q

  日期：2011.9.14

  glycopeptides derived from α-DG by a strategy in which properly protected phospho-mannosides are coupled with a Fmoc protected threonine derivative, followed by the use of the resulting derivatives in automated solid-phase glycopeptide synthesis using hyper-acid-sensitive Sieber amide resin. Synthetic efforts also provided a reduced phospho-trisaccharide, and the NMR data of this derivative confirmed the proper

  α-dystroglycan (α-DG) 的异常糖基化导致与细胞外基质相互作用的丧失，并且是多种疾病发病机制的核心。为了检查 α-DG 的蛋白质糖基化，已经开发了一种简便的合成方法，用于通过适当保护的磷酸甘露糖苷与 Fmoc 保护的苏氨酸衍生物偶联的策略，制备源自 α-DG 的罕见磷酸化 O-甘露糖基糖肽，随后将所得衍生物用于使用对酸敏感的 Sieber 酰胺树脂的自动固相糖肽合成。合成工作还提供了一种还原的磷酸三糖，该衍生物的 NMR 数据证实了不寻常的磷酸聚糖结构的正确结构分配。糖肽使探索调节关键聚糖加工的因素成为可能。已确定具有 6-磷酸-O-甘露糖残基的糖肽不是酶 POMGnT1 作用的受体，POMGnT1 将 β(1,2)-GlcNAc 连接到 O-甘露糖基部分，而未磷酸化的衍生物很容易延伸通过酶。这一发现暗示了确定 O-聚糖结构命运的特定事件序列。还发现 POMGnT1 的活
• [EN] DISACCHARIDES<br/>[FR] DISACCHARIDES
  申请人：ALIMENTARY HEALTH LTD

  公开号：WO2010049921A1

  公开（公告）日：2010-05-06

  A disaccharide having the structure (Formula I), and a disaccharide having the structure (Formula II) exhibit immunomodulatory activity.

  具有结构（公式I）的二糖和具有结构（公式II）的二糖表现出免疫调节活性。
• Synthesis and study of the glycosyl-donor properties of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline
  作者：Sergey S. Pertel、Elena S. Kakayan、Alexander I. Zinin、Leonid O. Kononov

  DOI：10.1016/j.carres.2024.109040

  日期：2024.2

  A synthesis of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline – a previously unknown 2-alkoxy glyco-[2,1-d]-2-oxazoline derivative with d-galacto configuration was carried out. Glycosylating activity of the obtained galactooxazoline has been studied and it has been shown that in the presence of a weak protic acid, such as sym-collidinium triflate, this

  2-(2,2,2-三氯乙氧基)-(3,4,6-三-O-乙酰基-1,2-二脱氧基-α- d-吡喃半乳糖)-[2,1- d ]-2的合成-恶唑啉–一种以前未知的具有d-半乳糖构型的 2-烷氧基糖-[2,1- d ]-2-恶唑啉衍生物。对所得半乳恶唑啉的糖基化活性进行了研究，结果表明，在弱质子酸（例如sym -collidinium triflate）存在下，该物质表现出反应性和 1,2-反式立体选择性糖基供体的特性。已发现糖的恶唑啉衍生物的均聚反应在相同条件下进行，导致假低聚糖产物的形成。人们发现，这种不希望的副反应可以通过改变酸催化剂浓度来抑制，从而开发出使用合成的2-(2,2, 2-三氯乙氧基)-2-恶唑啉糖基供体在非常温和的条件下。
• Direct Synthesis of Glycosyl Chlorides from Thioglycosides
  作者：Daniel J. Hoard、Yogesh Sutar、Alexei V. Demchenko

  DOI：10.1021/acs.joc.4c00244

  日期：2024.5.17

  Reported herein is a new method for the direct synthesis of glycosyl chlorides from thioglycosides using sulfuryl chloride at rt. A variety of thioglycosides and thioimidates could be used as substrates. Both acid- and base-sensitive protecting groups were found compatible with these reaction conditions. Preliminary investigation of the reaction mechanism indicates chlorination of the leaving group

  本文报道了一种在 rt 下使用硫酰氯从硫代糖苷直接合成糖基氯的新方法。多种硫代糖苷和硫代亚胺酸盐可用作底物。发现酸敏感和碱敏感保护基团都与这些反应条件相容。对反应机理的初步研究表明，异头硫处离基的氯化是反应的关键步骤。