3,4,6-tri-O-benzyl-D-mannono-1,5-lactone | 852459-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-D-mannono-1,5-lactone
• 英文别名: (3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one
• CAS: 852459-74-6
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: FRWRDFOHUINWHU-XDZVQPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-D-mannono-1,5-lactone 在 palladium dihydroxide aluminum oxide 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 1-deoxy-α-D-galacto-hept-2-ulosyl-(2->2)-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：

  3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 在 N-碘代丁二酰亚胺 、 氨 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 135.5h， 生成 3,4,6-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

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。
• 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
  作者：Rie Namme、Takashi Mitsugi、Hideyo Takahashi、Moto Shiro、Shiro Ikegami

  DOI：10.1016/j.tet.2006.07.032

  日期：2006.9

  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.