3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone | 912650-33-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone
• CAS: 912650-33-0
• 化学式: C₆₂H₆₄O₁₁
• 分子量: 985.184
• InChiKey: FSFKRXLSGPDAME-GQYCUAKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.77
• 重原子数：
  73.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  109.37
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 在 palladium dihydroxide aluminum oxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以100%的产率得到1-deoxy-α-D-gluco-hept-2-ulosyl-(2->2)-D-glucono-1,5-lactone
  参考文献：
  名称：

  Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

  摘要：

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.032
• 作为产物：
  描述：

  1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.5h， 生成 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone
  参考文献：
  名称：

  Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

  摘要：

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.032