phenylthio 2-deoxy-α-D-galactoside | 1258871-04-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenylthio 2-deoxy-α-D-galactoside
• 英文别名: (2R,3R,4R,6R)-2-(hydroxymethyl)-6-phenylsulfanyloxane-3,4-diol
• CAS: 1258871-04-3
• 化学式: C₁₂H₁₆O₄S
• 分子量: 256.323
• InChiKey: BAMFXEDMVPTGQV-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenylthio 2-deoxy-α-D-galactoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 4.08h， 生成 2-phenylethyl 2-deoxy-α-D-galactopyranoside 、 2-phenylethyl 2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

  摘要：

  使用单电子转移（SET）机制，在长波长紫外照射下，使用2,3-二氯-5,6-二氰基-对苯醌（DDQ）有效实现了几种未保护的脱氧硫代糖苷和醇的O-糖基化。在某些情况下，使用对甲氧基硼酸对未受保护的糖基供体的 1,3-二醇（C4 和 C6 位）进行临时保护非常有效，从而提高了所获得的 O-糖苷的产率。

  DOI：

  10.1039/c3ob41143e
• 作为产物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-D-galactopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 C₁₂H₁₆O₄S 、 phenylthio 2-deoxy-α-D-galactoside
  参考文献：
  名称：

  Design and synthesis of functionalized trisaccharides as p53-peptide mimics

  摘要：

  Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an alpha-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.012

文献信息

• Design and synthesis of functionalized trisaccharides as p53-peptide mimics
  作者：Kaori Sakurai、Daniel Kahne

  DOI：10.1016/j.tetlet.2010.05.012

  日期：2010.7

  Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an alpha-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology. (C) 2010 Elsevier Ltd. All rights reserved.
• Light-induced O-glycosylation of unprotected deoxythioglycosyl donors
  作者：Mayuka Nakanishi、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c3ob41143e

  日期：——

  The O-glycosylation of several unprotected deoxythioglycosides and alcohols using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under long-wavelength UV irradiation was effectively realized using a single electron transfer (SET) mechanism. In some cases, the use of p-methoxyboronic acid was very effective in temporary protection of the 1,3-diol (C4 and C6 positions) of the unprotected glycosyl donors to increase the yields of the obtained O-glycosides.

  使用单电子转移（SET）机制，在长波长紫外照射下，使用2,3-二氯-5,6-二氰基-对苯醌（DDQ）有效实现了几种未保护的脱氧硫代糖苷和醇的O-糖基化。在某些情况下，使用对甲氧基硼酸对未受保护的糖基供体的 1,3-二醇（C4 和 C6 位）进行临时保护非常有效，从而提高了所获得的 O-糖苷的产率。