(2R,3R,6R)-2-(acetoxymethyl)-6-(((2R,3R,4R,5R,6S)-4,5-diacetoxy-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)thio)-3,6-dihydro-2H-pyran-3,5-diyl diacetate | 1020154-87-3

• 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: (2R,3R,6R)-2-(acetoxymethyl)-6-(((2R,3R,4R,5R,6S)-4,5-diacetoxy-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)thio)-3,6-dihydro-2H-pyran-3,5-diyl diacetate
• CAS: 1020154-87-3
• 化学式: C₃₀H₃₈O₁₄S
• 分子量: 654.689
• InChiKey: UNAHXAWBJZMGNP-RRRZGGQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  45.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  168.42
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  methyl 2,3-di-O-acetyl-6-O-benzyl-4-thio-α-D-glucopyranoside 、 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以65%的产率得到(2R,3R,6R)-2-(acetoxymethyl)-6-(((2R,3R,4R,5R,6S)-4,5-diacetoxy-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)thio)-3,6-dihydro-2H-pyran-3,5-diyl diacetate
  参考文献：
  名称：

  Synthesis of S-linked carbohydrate analogues via a Ferrier reaction

  摘要：

  In this work, the synthetic utility of the Ferrier reaction to access S-linked disaccharides and S-linked glycoamino acids has been probed. Significantly, entry to a range of 1,4- and 1,6-S-linked disaccharides has been achieved using glycals derived from glucose and galactose, and sulfur containing coupling partners derived from methyl alpha-D-glucopyranoside. Access to S-linked glycoamino acids and glycopeptides has also been achieved using protected cysteine and homocysteine coupling partners within the Ferrier reaction. Functionalisation of the Ferrier products, for example, via dihydroxylation using OsO4 or amino acid coupling, and deprotection of the targets have also been achieved. In this way, entry to materials of interest as mimics of biologically interesting disaccharides and glycopeptides has been realised, including targets derived from rare sugars such as talopyranose and gulopyranose. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.042