2,5,6-tri-O-benzoyl-3-O-(2,5,6-tri-O-benzoyl-3-deoxy-β-D-xylo-hexofuranosyl)-D-mannono-1,4-lactone | 218614-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5,6-tri-O-benzoyl-3-O-(2,5,6-tri-O-benzoyl-3-deoxy-β-D-xylo-hexofuranosyl)-D-mannono-1,4-lactone
• CAS: 218614-45-0
• 化学式: C₅₄H₄₄O₁₆
• 分子量: 948.934
• InChiKey: PRRZGAIRWOUYJU-NTRZEZSNSA-N

物化性质

• 沸点：
  966.466±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.412±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.03
• 重原子数：
  70.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  202.56
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2,5,6-tri-O-benzoyl-3-O-(2,5,6-tri-O-benzoyl-3-deoxy-β-D-xylo-hexofuranosyl)-D-mannono-1,4-lactone 在 diisoamyl borane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以90%的产率得到2,5,6-tri-O-benzoyl-3-O-(2,5,6-tri-O-benzoyl-3-deoxy-β-D-xylo-hexofuranosyl)-D-mannofuranose
  参考文献：
  名称：

  The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp

  摘要：

  A convenient synthesis of free beta-D-Galf-(1 --> 3)-D-Manp (8a) is reported. The disaccharide is present as external unit in the lipopeptidophosphoglycan (LPPG) of Trypanosoma cruzi and internally in the lipophosphoglycan (LPG) of Leishmania. Condensation of 2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone (1) with 1,2,3,5,6-penta-O-benzoyl-D-galactofuranose promoted by SnCl4, led to the B-glycosyl-lactone, a key intermediate for disaccharide 8a, readily obtained by successive reduction of the lactone with diisoamylborane and debenzoylation. As in the LPG of Leishmania the HO-3 group of the galactofuranose is glycosylated by alpha-D-Galp, we also synthesized 3-deoxy-beta D-xylo-hexofuranosyl-(1 --> 3)-D-Manp (8b) and p-nitrophenyl 3-deoxy-beta-D-xylo-hexofuranoside for studying the influence of HO-3 in the interaction with specific glycosidases. The disaccharide 8a, and its corresponding alditol, were good substrates for the beta-D-galactofuranosidase from Penicillium fellutanum, whereas the 3-deoxyglycosides were not hydrolyzed by the enzyme. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00214-6
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 吡啶 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 2,5,6-tri-O-benzoyl-3-O-(2,5,6-tri-O-benzoyl-3-deoxy-β-D-xylo-hexofuranosyl)-D-mannono-1,4-lactone
  参考文献：
  名称：

  The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp

  摘要：

  A convenient synthesis of free beta-D-Galf-(1 --> 3)-D-Manp (8a) is reported. The disaccharide is present as external unit in the lipopeptidophosphoglycan (LPPG) of Trypanosoma cruzi and internally in the lipophosphoglycan (LPG) of Leishmania. Condensation of 2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone (1) with 1,2,3,5,6-penta-O-benzoyl-D-galactofuranose promoted by SnCl4, led to the B-glycosyl-lactone, a key intermediate for disaccharide 8a, readily obtained by successive reduction of the lactone with diisoamylborane and debenzoylation. As in the LPG of Leishmania the HO-3 group of the galactofuranose is glycosylated by alpha-D-Galp, we also synthesized 3-deoxy-beta D-xylo-hexofuranosyl-(1 --> 3)-D-Manp (8b) and p-nitrophenyl 3-deoxy-beta-D-xylo-hexofuranoside for studying the influence of HO-3 in the interaction with specific glycosidases. The disaccharide 8a, and its corresponding alditol, were good substrates for the beta-D-galactofuranosidase from Penicillium fellutanum, whereas the 3-deoxyglycosides were not hydrolyzed by the enzyme. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00214-6