N-(2-ethyldisulfanyl-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)acetamide | 232589-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-ethyldisulfanyl-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)acetamide
• 英文别名: ethyl 2-acetamido-2-deoxy-1-disulfide-β-D-glucopyranoside
• CAS: 232589-57-0
• 化学式: C₁₀H₁₉NO₅S₂
• 分子量: 297.397
• InChiKey: BEBPITOPHCOWDO-IGORNWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  99.02
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(2-ethyldisulfanyl-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)acetamide 在 三氟乙酸 作用下， 反应 18.0h， 生成 [3-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-1-methyl-3-phenyl-propylamino]-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：

  ethyl 2,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl disulfide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到N-(2-ethyldisulfanyl-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)acetamide
  参考文献：
  名称：

  Solid-Phase Synthesis of Thio-oligosaccharides

  摘要：

  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.

  DOI：

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

文献信息

• [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
• Glyco-SeS: Selenenylsulfide-Mediated Protein Glycoconjugation—A New Strategy in Post-Translational Modification
  作者：David P. Gamblin、Philippe Garnier、Sander van Kasteren、Neil J. Oldham、Antony J. Fairbanks、Benjamin G. Davis

  DOI：10.1002/anie.200352975

  日期：2004.2.6