methyl 2,3,4-tri-O-acetyl-6-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-thio-α-D-glucopyranoside | 106709-35-7

• 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-β-D-glucopyranosyl)-6-thio-α-D-glucopyranoside
• 英文别名: Methyl-<6-S-β-D-glucopyranosyl-6-thio-α-D-glucopyranosid>-heptaacetat；Methyl-(6-S-β-D-glucopyranosyl-6-thio-α-D-glucopyranosid)-heptaacetat；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methylsulfanyl]oxan-2-yl]methyl acetate
• CAS: 106709-35-7
• 化学式: C₂₇H₃₈O₁₇S
• 分子量: 666.655
• InChiKey: CZSKWESKPFKTTM-OTEFYFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  45
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  2-(2,3,4,6-四邻乙酰基-beta-d-吡喃葡萄糖)-2-硫代异脲氢溴酸 、 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.05h， 以70%的产率得到methyl 2,3,4-tri-O-acetyl-6-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Microwave Irradiation for Accelerating the Synthesis of Thioglycosides

  摘要：

  A simple and efficient procedure for the synthesis of thioglycosides has been achieved from the reaction of glycosylisothiouronium salts with alkyl or heteroaryl halides under microwave irradiation, in much shorter times and in yields comparable with conventional methods.

  DOI：

  10.1080/00397910600767314

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.