methyl 2,3,4-tri-O-acetyl-6-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-thio-α-D-glucopyranoside | 1020154-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-thio-α-D-glucopyranoside
• CAS: 1020154-88-4
• 化学式: C₂₇H₃₈O₁₇S
• 分子量: 666.655
• InChiKey: CZSKWESKPFKTTM-RKXFVDKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  45.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-thio-α-D-glucopyranoside 在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以100%的产率得到methyl 6-S-(α-D-mannopyranosyl)-6-thio-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-S-(4,6-di-O-acetyl-D-mannopyranosyl)-6-thio-α-D-glucopyranoside 、 乙酸酐 在 吡啶 作用下， 以42 mg的产率得到methyl 2,3,4-tri-O-acetyl-6-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-thio-α-D-glucopyranoside
  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

文献信息

• Streamlined Iterative Assembly of Thio‐Oligosaccharides by Aqueous <i>S</i> ‐Glycosylation of Diverse Deoxythio Sugars
  作者：Peng Wen、Peijing Jia、Qiuhua Fan、Bethany J. McCarty、Weiping Tang

  DOI：10.1002/cssc.202102483

  日期：2022.2.8

  Step by step: A streamlined practical iterative synthesis of S-oligosaccharides is developed in aqueous solution without the need of protecting any of the hydroxy groups. Various deoxythio sugar building blocks can be prepared efficiently. The Ca(OH)2-promoted aqueous S-glycosylation can be realized with high chemo- and stereoselectivity.

  一步一步：在水溶液中开发了S-低聚糖的简化实用迭代合成，无需保护任何羟基。可以有效地制备各种脱氧硫代糖结构单元。 Ca(OH) 2 -促进的水性S-糖基化可以以高化学选择性和立体选择性实现。
• Photoinduced Thiol−Ene Coupling as a Click Ligation Tool for Thiodisaccharide Synthesis
  作者：Michele Fiore、Alberto Marra、Alessandro Dondoni

  DOI：10.1021/jo900514w

  日期：2009.6.5

  The high efficiency and selectivity of the thiol-ene radical reaction has been validated by the photoinduced coupling of anomeric sugar thiols with sugar alkenes to give 1,6-linked S-disaccharides in good to excellent yields (76-92%) and high diastereoselectivities (up to 99%). The reaction appears to be well-qualified as an exemplar click process.