2,3-di-O-benzyl-α-D-mannopyranoside | 145350-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzyl-α-D-mannopyranoside
• 英文别名: 2,3-di-O-benzyl-α-D-mannopyranose；(2S,3S,4S,5R,6R)-6-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxane-2,5-diol
• CAS: 145350-27-2
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: SEJPLCXOYKLKOZ-SLHNCBLASA-N

物化性质

• 沸点：
  562.1±50.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-α-D-mannopyranoside 在 吡啶 、 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1,4-di-O-acetyl-2,3-di-O-benzyl-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  Synthetic Studies on Oligosaccharide of a Glycolipid from the Spermatozoa of Bivalves. VII. The Synthesis of Di-, Tri-, Tetrasaccharides Related to Glycosphinogolipid.

  摘要：

  构成脂质 IV 部分结构（1）的三种寡糖合成如下。二糖 O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (13)，三糖 O-α-D-mannopyranosyl-(1→3)-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (21)、和四糖 O-α-D-吡喃甘露糖基-(1→3)-O-[β-D-吡喃木糖基-(1→2)]-O-β-D-吡喃甘露糖基-(1→4)-D-吡喃葡萄糖（25）都是通过逐步缩合适当保护的单糖单元合成的。1，6-脱水-D-吡喃葡萄糖衍生物用作糖基受体，D-甘露糖和 D-木糖的溴化物衍生物用作供体。

  DOI：

  10.1248/cpb.40.1930
• 作为产物：
  描述：

  2,2,2-trichloroethyl 4,6-O-benzylidene-α-D-mannopyranoside 在 四丁基溴化铵 、 sodium hydride 、 copper(II) sulfate 、 溶剂黄146 、 锌 作用下， 以 乙酸酐 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2,3-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthetic Studies on Oligosaccharide of a Glycolipid from the Spermatozoa of Bivalves. VII. The Synthesis of Di-, Tri-, Tetrasaccharides Related to Glycosphinogolipid.

  摘要：

  构成脂质 IV 部分结构（1）的三种寡糖合成如下。二糖 O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (13)，三糖 O-α-D-mannopyranosyl-(1→3)-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (21)、和四糖 O-α-D-吡喃甘露糖基-(1→3)-O-[β-D-吡喃木糖基-(1→2)]-O-β-D-吡喃甘露糖基-(1→4)-D-吡喃葡萄糖（25）都是通过逐步缩合适当保护的单糖单元合成的。1，6-脱水-D-吡喃葡萄糖衍生物用作糖基受体，D-甘露糖和 D-木糖的溴化物衍生物用作供体。

  DOI：

  10.1248/cpb.40.1930

文献信息

• Method of forming glycosidic bonds from thioglycosides using an N,N-dialkylsulfinamide
  申请人：——

  公开号：US20040019198A1

  公开（公告）日：2004-01-29

  A method of forming a glycosidic bond utilizing an activated thioglycoside is disclosed. The thioglycoside is activated by an N,N-dialkylsulfinamide and trifluoromethanesulfonic anhydride. The method allows the facile synthesis of disaccharides, oligosacchraides, and polysaccharides in solution or on a polymer support.

  揭示了一种利用活化硫代糖苷键的方法。该硫代糖苷经N,N-二烷基亚磺酰胺和三氟甲磺酸酐激活。该方法允许在溶液中或在聚合物支撑上轻松合成二糖、寡糖和多糖。
• A unique approach to the synthesis of a dengue vaccine and the novel tetrasaccharide that results
  作者：Nigel Kevin Jalsa、Gurdial Singh

  DOI：10.1016/j.tetasy.2009.02.024

  日期：2009.5

  An approach to the development of a dengue vaccine by synthesizing the hexasaccharide epitope on the viral surface is examined. The stereochemical and structural challenges include the synthesis of a beta-mannoside bond. Synthesis of this bond is approached via a trisaccharide analogue portion of the epitope. A novel tetrasaccharide with a mannose-mannose anomeric linkage results in the Course of the synthetic attempts. (C) 2009 Elsevier Ltd. All rights reserved.
• US6960654B2
  申请人：——

  公开号：US6960654B2

  公开（公告）日：2005-11-01
• Synthetic Studies on Oligosaccharide of a Glycolipid from the Spermatozoa of Bivalves. VII. The Synthesis of Di-, Tri-, Tetrasaccharides Related to Glycosphinogolipid.
  作者：Tadahiro TAKEDA、Noriyasu HADA、Yukio OGIHARA

  DOI：10.1248/cpb.40.1930

  日期：——

  The three kinds of oligosaccharides that constitute the partial structure of lipid IV (1) were synthesized as follows. The disaccharide O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (13), the trisaccharide O-α-D-mannopyranosyl-(1→3)-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (21), and the tetrasaccharide O-α-D-mannopyranosyl-(1→3)-O-[β-D-xylopyranosyl-(1→2)]-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (25) were each synthesized by stepwise condensation of suitably protected monosaccharide units. A 1, 6-anhydro-D-glucopyranose derivative was used as the glycosyl acceptor, and bromide derivatives of D-mannose and D-xylose as donors.

  构成脂质 IV 部分结构（1）的三种寡糖合成如下。二糖 O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (13)，三糖 O-α-D-mannopyranosyl-(1→3)-O-β-D-mannopyranosyl-(1→4)-D-glucopyranose (21)、和四糖 O-α-D-吡喃甘露糖基-(1→3)-O-[β-D-吡喃木糖基-(1→2)]-O-β-D-吡喃甘露糖基-(1→4)-D-吡喃葡萄糖（25）都是通过逐步缩合适当保护的单糖单元合成的。1，6-脱水-D-吡喃葡萄糖衍生物用作糖基受体，D-甘露糖和 D-木糖的溴化物衍生物用作供体。