benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 107855-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 107855-12-9
• 化学式: C₅₄H₅₅NO₁₅
• 分子量: 958.028
• InChiKey: JALYECPXKKZBNU-MQBIJBGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  70.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  180.89
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 benzyl O-(2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Studies on the Fast Atom Bombardment Mass Spectrometry Fragmentation of Amino Sugars Using Synthetic Derivatives of the Trisaccharide Unit β-D-Glucopyranosyl-(1-3)-O-2-deoxy-2-amino-β-d-glucopyranosyl-(1-4)-O-d-glucopyranose

  摘要：

  N-Phthaloyl, N-acetyl, N-benzyl, N-acetyl-N-methyl, N,N-dimethyl, N-benzoyl, and N,N-dibenzoyl derivatives of the trisaccharide beta-D-glucopyranosyl-(1-3)-O-(2-deoxy-2-amino-beta-D-glucopyranosyl)-( 1-4)-O-beta-D-glucopyranose were synthesized and analyzed by FAB MS. The intensity ratios of the peaks resulting from cleavage of the anomeric bond of the glucosamine residue and the respective molecular ion peaks turned out to be high for the N-acyl derivatives and up to two orders of magnitude lower for the N-alkyl compounds. These results show that fragmentation at the anomeric carbon of the amino sugar may be assisted by the carbonyl group and the resulting cation is stabilized by delocalization of the positive charge.

  DOI：

  10.1080/07328309808001890
• 作为产物：
  描述：

  benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 盐酸 、 3 Angstroems MS 、 4 Angstroems MS 、 三氟化硼乙醚 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Studies on the Fast Atom Bombardment Mass Spectrometry Fragmentation of Amino Sugars Using Synthetic Derivatives of the Trisaccharide Unit β-D-Glucopyranosyl-(1-3)-O-2-deoxy-2-amino-β-d-glucopyranosyl-(1-4)-O-d-glucopyranose

  摘要：

  N-Phthaloyl, N-acetyl, N-benzyl, N-acetyl-N-methyl, N,N-dimethyl, N-benzoyl, and N,N-dibenzoyl derivatives of the trisaccharide beta-D-glucopyranosyl-(1-3)-O-(2-deoxy-2-amino-beta-D-glucopyranosyl)-( 1-4)-O-beta-D-glucopyranose were synthesized and analyzed by FAB MS. The intensity ratios of the peaks resulting from cleavage of the anomeric bond of the glucosamine residue and the respective molecular ion peaks turned out to be high for the N-acyl derivatives and up to two orders of magnitude lower for the N-alkyl compounds. These results show that fragmentation at the anomeric carbon of the amino sugar may be assisted by the carbonyl group and the resulting cation is stabilized by delocalization of the positive charge.

  DOI：

  10.1080/07328309808001890

文献信息

• An efficient approach to O-glycosides through CuBr2-Bu4NBr mediated activation of glycosides
  作者：Susumu Sato、Masato Mori、Yukishige Ito、tomoya Ogawa

  DOI：10.1016/s0008-6215(00)90163-0

  日期：1986.11