(2,3-di-O-benzoyl-β-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl) 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 917368-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3-di-O-benzoyl-β-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl) 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-5-benzoyloxy-3-hydroxy-2-(hydroxymethyl)-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxan-4-yl] benzoate
• CAS: 917368-41-3
• 化学式: C₄₆H₅₄O₂₅
• 分子量: 1006.92
• InChiKey: FBYGGURTLDHXCO-ZORQJBRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  71
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  323
• 氢给体数：
  2
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  (2,3-di-O-benzoyl-β-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl) 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 、 methyl2,2-bis (ethylthio) propanoate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以55%的产率得到(2,3-di-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-β-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl) 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of pyruvate ketals of carbohydrates

  摘要：

  An efficient method for the preparation of pyruvate ketals of carbohydrates has been developed using N-iodosuccinimide or 1,3-dibromo-5,5-dimethylhydantoin as activator and methyl 2,2-di(ethylthio)propionate. The method has been applied for the preparation of a pyruvate ketal-containing trisaccharide present in the bacterial cell-wall of Mycobacterium smegmatis. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2006.09.159
• 作为产物：
  描述：

  (2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl) 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 高氯酸 、 silica gel 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以95%的产率得到(2,3-di-O-benzoyl-β-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl) 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of pyruvate ketals of carbohydrates

  摘要：

  An efficient method for the preparation of pyruvate ketals of carbohydrates has been developed using N-iodosuccinimide or 1,3-dibromo-5,5-dimethylhydantoin as activator and methyl 2,2-di(ethylthio)propionate. The method has been applied for the preparation of a pyruvate ketal-containing trisaccharide present in the bacterial cell-wall of Mycobacterium smegmatis. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2006.09.159