benzoxazolyl-3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-1-thio-β-D-glucopyranoside | 930102-44-6

• 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-trifluoroacetamido-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-trifluoroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 930102-44-6
• 化学式: C₂₁H₂₁F₃N₂O₉S
• 分子量: 534.467
• InChiKey: PAIZPLAEHZDPFO-ZKXLYKBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  169
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  benzoxazolyl-3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-1-thio-β-D-glucopyranoside 、 甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 以86%的产率得到methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-β-D-glucopyranosyl)-(1->4)-2,3,6-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：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoracetamido-β-D-glucopyranoside 在 18-冠醚-6 、 1,1-二氯甲醚 、 zinc(II) chloride 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 2.0h， 生成 benzoxazolyl-3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-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