benzoxazolyl-3,4,6-tri-O-acetyl-2-deoxy-2-trichloroethoxycarbamoyl-1-thio-β-D-glucopyranoside | 930102-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzoxazolyl-3,4,6-tri-O-acetyl-2-deoxy-2-trichloroethoxycarbamoyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-(1,3-benzoxazol-2-ylsulfanyl)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 930102-43-5
• 化学式: C₂₂H₂₃Cl₃N₂O₁₀S
• 分子量: 613.857
• InChiKey: JMDHGCFVDCJVKS-NNIGNNQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  benzoxazolyl-3,4,6-tri-O-acetyl-2-deoxy-2-trichloroethoxycarbamoyl-1-thio-β-D-glucopyranoside 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 三氟甲烷磺酸甲酯 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroethoxycarbamoyl-β-D-glucopyranosyl)-(1->6)-(3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Chemoselective Synthesis of Oligosaccharides of 2-Deoxy-2-aminosugars

  摘要：

  Along with the application of the S-benzoxazolyl glycosides to the high-yielding synthesis of disaccharides of the 2-amino-2-deoxy series, chemoselective assembly of oligosaccharides containing multiple residues of 2-amino-2-deoxyglycoses is reported. This modified armed-disarmed approach is relying on the observation that 2-N-trichloroethoxycarbonyl derivatives of S-benzoxazolyl glycosides are significantly more reactive than their 2-N-phthaloyl counterparts in MeOTf-promoted glycosylations. This allowed efficient chemoselective synthesis of 1,2-trans-linked oligosaccharides, the disarmed reducing end of which can be activated for immediate second step glycosidation in the presence of a more powerful activator, AgOTf. As a result of this two-step activation, trans-trans-patterned trisaccharides could be assembled in a highly efficient manner. This result differs from the classic armed-disarmed technique, according to which usually cis-trans-patterned oligosaccharides are generated.

  DOI：

  10.1021/jo062171d
• 作为产物：
  描述：

  potassium 2-mercaptobenzoxazolate 、 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide 在 18-冠醚-6 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以73%的产率得到benzoxazolyl-3,4,6-tri-O-acetyl-2-deoxy-2-trichloroethoxycarbamoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoselective Synthesis of Oligosaccharides of 2-Deoxy-2-aminosugars

  摘要：

  Along with the application of the S-benzoxazolyl glycosides to the high-yielding synthesis of disaccharides of the 2-amino-2-deoxy series, chemoselective assembly of oligosaccharides containing multiple residues of 2-amino-2-deoxyglycoses is reported. This modified armed-disarmed approach is relying on the observation that 2-N-trichloroethoxycarbonyl derivatives of S-benzoxazolyl glycosides are significantly more reactive than their 2-N-phthaloyl counterparts in MeOTf-promoted glycosylations. This allowed efficient chemoselective synthesis of 1,2-trans-linked oligosaccharides, the disarmed reducing end of which can be activated for immediate second step glycosidation in the presence of a more powerful activator, AgOTf. As a result of this two-step activation, trans-trans-patterned trisaccharides could be assembled in a highly efficient manner. This result differs from the classic armed-disarmed technique, according to which usually cis-trans-patterned oligosaccharides are generated.

  DOI：

  10.1021/jo062171d

文献信息

• Application of Glycosyl Thioimidates in Solid-Phase Oligosaccharide Synthesis
  作者：M. Cristina Parlato、Medha N. Kamat、Haisheng Wang、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1021/jo701902f

  日期：2008.3.1

  S-benzoxazolyl (SBox) and S-thiazolinyl (STaz) glycosides, were investigated as glycosyl donors for solid-phase oligosaccharide synthesis. It was demonstrated that these derivatives are suitable for both glycosyl acceptor-bound and glycosyl donor-bound strategies, commonly employed in resin-supported oligosaccharide synthesis.

  研究了两类稳定的硫代酰亚胺基衍生物，即S-苯并恶唑基（SBox）和S-噻唑啉基（STaz）糖苷，作为固相寡糖合成的糖基供体。已证明这些衍生物既适用于糖基受体结合的策略，也适用于糖基供体结合的策略，通常用于树脂支持的寡糖合成中。