2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-D-galactono-1,4-lactone | 129728-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-D-galactono-1,4-lactone
• CAS: 129728-04-7
• 化学式: C₈₈H₇₀O₂₆
• 分子量: 1543.51
• InChiKey: DGCGCOXNBGKPCJ-KLJGDBTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.28
• 重原子数：
  114.0
• 可旋转键数：
  30.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  326.22
• 氢给体数：
  0.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-D-galactono-1,4-lactone 在 二(3-甲基丁烷-2-基)硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-β-D-galactofuranose 、 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-α-D-galactofuranose
  参考文献：
  名称：

  Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose

  摘要：

  Benzoylation of D-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23 degrees, gave the 2,6-dibenzoate (2, 62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-alpha,beta-D-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl)-D - galactono-1,4-lactone (4, 70%), HO-3 of which was benzoylated to give 5. The structure of 4 was confirmed by its conversion into crystalline beta-D-Galf-(1----5)-D-Gal-ol (8). Reduction of the lactone function of 5 with di-isoamylborane followed by debenzoylation gave beta-D-Galf-(1----5)-D-Galf (7). A by-product of the condensation of 1 with 2 was characterized as 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranos yl)-D- galactono-1,4-lactone (9), which was converted, as for 5, into beta-D-Galf-(1----3)[beta-D-Galf-(1----5)]-D-Galf (13).

  DOI：

  10.1016/0008-6215(90)84193-x
• 作为产物：
  描述：

  2,6-di-O-benzoyl-D-galactono-1,4-lactone 、 1,2,3,5,6-penta-o-benzoylhexofuranose 在 四氯化锡 作用下， 生成 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-D-galactono-1,4-lactone 、 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside
  参考文献：
  名称：

  Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose

  摘要：

  Benzoylation of D-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23 degrees, gave the 2,6-dibenzoate (2, 62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-alpha,beta-D-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl)-D - galactono-1,4-lactone (4, 70%), HO-3 of which was benzoylated to give 5. The structure of 4 was confirmed by its conversion into crystalline beta-D-Galf-(1----5)-D-Gal-ol (8). Reduction of the lactone function of 5 with di-isoamylborane followed by debenzoylation gave beta-D-Galf-(1----5)-D-Galf (7). A by-product of the condensation of 1 with 2 was characterized as 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranos yl)-D- galactono-1,4-lactone (9), which was converted, as for 5, into beta-D-Galf-(1----3)[beta-D-Galf-(1----5)]-D-Galf (13).

  DOI：

  10.1016/0008-6215(90)84193-x