ethyl 2,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl disulfide | 232589-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl disulfide
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(ethyldisulfanyl)oxan-2-yl]methyl acetate
• CAS: 232589-56-9
• 化学式: C₁₆H₂₅NO₈S₂
• 分子量: 423.508
• InChiKey: YLTOEVHCMNUERE-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl disulfide 在 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 [3-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cycloheptylamino]-acetic acid
  参考文献：
  名称：

  Solid‐Phase Synthesis of a 1‐Thio‐β‐d‐GlcNAc Carbohydrate Mimetic Library

  摘要：

  The solid phase synthesis of N-acetyl-2-deoxy-1-thio-beta-D-glucopyranoside derivatives by reacting an immobilized sugar thiol with Michael acceptors and alpha-chloroketones, followed by ketone reductions, reductive aminations, acylations and alkylations was developed to yield a library of 1088 compounds. Such carbohydrate mimetic libraries are synthesized efficiently on the solid phase without the need for protection of the sugar hydroxyl groups. The library was designed for the identification of potential inhibitors Of beta-D-GlcNAc binding proteins.

  DOI：

  10.1081/car-120026475
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-1-硫代-beta-D-吡喃葡萄糖 3,4,6-三乙酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl disulfide
  参考文献：
  名称：

  Glyco-SeS：亚硒硫醚介导的蛋白质糖缀合——一种翻译后修饰的新策略。

  摘要：

  DOI：

  10.1002/anie.200352975

文献信息

• Reagents And Methods For The Formation Of Disulfide Bonds And The Glycosylation Of Proteins
  申请人：Davis Guy Benjamin

  公开号：US20070213506A1

  公开（公告）日：2007-09-13

  Methods and reagents for the formation of disulfide bonds, particularly in proteins, peptides and amino acids. The methods and reagents are particularly useful for the controlled glycosylation of proteins, peptides and amino acids. The methods utilise thiosulfonate or selenenylsulfide compounds as reagents or intermediates. Some proteins and peptides comprising selenenyl-sulfide groups also form part of the invention.

  本发明涉及在蛋白质、肽和氨基酸中形成二硫键的方法和试剂，特别是用于蛋白质、肽和氨基酸的可控糖基化。所述方法利用硫代磺酸盐或硒酰硫酸盐化合物作为试剂或中间体。一些含有硒酰硫酸盐基团的蛋白质和肽也是本发明的一部分。
• [EN] REAGENTS AND METHODS FOR THE FORMATION OF DISULFIDE BONDS AND THE GLYCOSYLATION OF PROTEINS<br/>[FR] REACTIFS ET PROCEDES POUR FORMER DES LIAISONS DISULFURE ET POUR GLYCOSYLER DES PROTEINES
  申请人：ISIS INNOVATION

  公开号：WO2005000862A3

  公开（公告）日：2005-08-18
• Solid-Phase Synthesis of Thio-oligosaccharides
  作者：Gerd Hummel、Ole Hindsgaul

  DOI：10.1002/(sici)1521-3773(19990614)38:12<1782::aid-anie1782>3.0.co;2-1

  日期：1999.6.14

  No protecting groups are present in the highly reactive polymer-bound sugar 1-thiolates 1, which undergo reactions with sugar triflates 2 to give thio-oligosaccharides 3 in high yield. Tr=trityl=triphenylmethyl, Tf=trifluoromethylsulfonyl, Bz=benzoyl.
• REAGENTS AND METHODS FOR THE FORMATION OF DISULFIDE BONDS AND THE GLYCOSYLATION OF PROTEINS
  申请人：ISIS INNOVATION LIMITED

  公开号：EP1644390A2

  公开（公告）日：2006-04-12
• US8637578B2
  申请人：——

  公开号：US8637578B2

  公开（公告）日：2014-01-28