benzyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranoside | 70056-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranoside
• 英文别名: Benzyl-6-O-acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranosid
• CAS: 70056-69-8
• 化学式: C₃₆H₃₈O₇
• 分子量: 582.694
• InChiKey: YEELBAWKPSBSET-DQROVBKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  benzyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以75%的产率得到benzyl 2,3,4-tri-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  An expedient synthesis of benzyl 2,3,4-tri-O-benzyl-β-d-glucopyranoside and benzyl 2,3,4-tri-O-benzyl-β-d-mannopyranoside

  摘要：

  An efficient three-step synthesis of benzyl 2,3,4-tri-O-benzyl-beta-D-glucopyranoside, a widely used building block in carbohydrate chemistry, is described. The key step is the selective debenzylation-acetylation of perbenzylated beta-glucose using ZnCl2-Ac2O-HOAc. This approach was also used to affect an efficient three-step synthesis of benzyl 2,3,4-tri-O-benzyl-beta-D-mannopyranoside. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.013
• 作为产物：
  描述：

  1,6-二-O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃甘露糖 在 calcium sulfate 、 氢溴酸 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 benzyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  Paulsen, Hans; Lockhoff, Oswald, Chemische Berichte, 1981, vol. 114, # 9, p. 3102 - 3114

  摘要：

  DOI：

文献信息

• A Novel Selectfluor-Mediated Regioselective <i>O</i>-Benzyl Ether Acetolysis of Perbenzylated Monosaccharides
  作者：Marlon S. Tambie、Nigel Kevin Jalsa

  DOI：10.1080/07328303.2015.1108423

  日期：2015.11.22

  Selectfluor, a source of the super electrophile F+, has replaced conventional reagents that supply F+ for fluorination due to its attractive physical and chemical properties. This study is the first report of using Selectfluor as a debenzylating reagent. Selectfluor has been found to effect regioselective O- benzyl acetolysis from the per-O-benzylated derivatives of glucose and mannose, which are among the most commonly occurring monosaccharides. For both derivatives, one equivalent of Selectfluor first cleaves the primary benzyl, while a second equivalent subsequently removes the anomeric benzyl. Regioselective removal at higher equivalents proved difficult, with complex mixtures being obtained. The reaction proceeded under mild conditions with good yields and high regioselectivity, resulting in quick access to partially benzylated monosaccharide derivatives. This study provides shortened access to attractive building blocks for oligosaccharide synthesis.