2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-D-mannono-1,5-lactone | 852459-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-D-mannono-1,5-lactone
• CAS: 852459-70-2
• 化学式: C₃₅H₃₆O₇
• 分子量: 568.667
• InChiKey: DLLMIGSGQJBJJJ-WZJLIZBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-D-mannono-1,5-lactone 在 三氟甲磺酸 、 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->3)-2,4,6-tri-O-benzyl-D-mannono-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：

  allyl D-mannopyranoside 在 potassium tert-butylate 、 乙酸酐 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 119.0h， 生成 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-D-mannono-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

文献信息

• Synthesis of PI-88 analogue using novel O-glycosidation of exo-methylenesugars
  作者：Rie Namme、Takashi Mitsugi、Hideyo Takahashi、Shiro Ikegami

  DOI：10.1016/j.tetlet.2005.03.016

  日期：2005.4

  Acid-promoted α-stereoselective O-glycosidation of 1-exo-methylenesugars was successfully applied to the synthesis of a PI-88 analogue. By using methanesulfonic acid as a promoter, 1′-C-methyl-α-disaccharides with p-methoxybenzyl protection were obtained in high yield. The sequence of selective deprotection and glycosidation provided 1-C-methyl-pentasaccharide efficiently.

  酸性促进的1- exo-亚甲基糖的α-立体选择性O-糖基化已成功应用于PI-88类似物的合成。通过使用甲磺酸作为促进剂，可以高收率得到具有对甲氧基苄基保护的1' - C-甲基-α-二糖。选择性脱保护和糖苷化的序列有效地提供了1 - C-甲基五糖。