benzoxazolyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 930102-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzoxazolyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-4-acetyloxy-6-(1,3-benzoxazol-2-ylsulfanyl)-5-(1,3-dioxoisoindol-2-yl)-2-(hydroxymethyl)oxan-3-yl] acetate
• CAS: 930102-54-8
• 化学式: C₂₅H₂₂N₂O₉S
• 分子量: 526.524
• InChiKey: SLWSYRJTUIYLJE-NQZVWWGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  171
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzoxazolyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-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：

  2-巯基苯并恶唑 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 水 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.5h， 生成 benzoxazolyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-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