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-glucopyranoside | 930102-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-[[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-(1,3-benzoxazol-2-ylsulfanyl)-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methoxy]-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 930102-56-0
• 化学式: C₄₀H₄₀Cl₃N₃O₁₈S
• 分子量: 989.192
• InChiKey: WZAOWQIZFUBBLW-NBDJJHNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  65
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  286
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  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-glucopyranoside 、 甲基2,3,4-三-O-苄基-α-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73%的产率得到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 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 32.5h， 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-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