phenyl 3,6-di-O-pivaloyl-1-thio-α-D-mannopyranoside | 210295-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,6-di-O-pivaloyl-1-thio-α-D-mannopyranoside
• 英文别名: pivaloyl(-3)[pivaloyl(-6)]Man(a)-SPh；[(2R,3R,4S,5S,6R)-4-(2,2-dimethylpropanoyloxy)-3,5-dihydroxy-6-phenylsulfanyloxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 210295-04-8
• 化学式: C₂₂H₃₂O₇S
• 分子量: 440.558
• InChiKey: YCAOXHKHNQVOLR-DFBDCSAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 3,6-di-O-pivaloyl-1-thio-α-D-mannopyranoside 在 四丁基碘化铵 、 氧化汞红 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以67%的产率得到phenyl 2,6-di-O-pivaloyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Cesium Trifluoroacetate or Silver Oxide Mediated Acyl Migration for the Construction of Disaccharide Building Blocks

  摘要：

  基于 CsO2CCF3 或 Ag2O 介导的酰基迁移，一种选择性区分吡喃糖苷的 2-OH 和 3-OH 的简便方法已经建立。2-OH 和 3-OH 可以依次被所需的碳水化合物糖基化，生成生物所需的二糖。提出了一种涉及酸或碱辅助酰基迁移的机制。

  DOI：

  10.1055/s-2006-933105
• 作为产物：
  描述：

  三甲基乙酰氯 、 苯基1-硫代吡喃己糖苷 以 吡啶 为溶剂， 反应 1.5h， 以90%的产率得到phenyl 3,6-di-O-pivaloyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains

  摘要：

  Synthetic routes are described to a partial structure common to all high mannose-type sugar chains and complex-type sugar chains based on a chemoenzymatic strategy which incorporates, (a) enzymatic synthesis of oligosaccharide blocks using glycosidases, and (b) chemical synthesis of the branching oligosaccharides via regioselective coupling. All reaction products correspond to key intermediates necessary for the construction of N-linked oligosaccharides and we have synthesized the branched tetra-manno-oligosaccharide high mannose-type sugar chain and the branched hexa-oligosaccharide complex-type sugar chain using this simple and direct method. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10001-5

文献信息

• Cesium Trifluoroacetate or Silver Oxide Mediated Acyl Migration for the Construction of Disaccharide Building Blocks
  作者：Cheng-Wei Tom Chang、Shenglou Deng

  DOI：10.1055/s-2006-933105

  日期：——

  A convenient method for the selective differentiation of the 2-OH and 3-OH of pyranosides, based on the CsO2CCF3- or Ag2O-mediated acyl migration, has been established. The 2-OH and 3-OH can be sequentially glycosylated by the desired carbohydrate generating disaccharides of biological interest. A mechanism involving either acid- or base-assisted acyl migration is proposed.

  基于 CsO2CCF3 或 Ag2O 介导的酰基迁移，一种选择性区分吡喃糖苷的 2-OH 和 3-OH 的简便方法已经建立。2-OH 和 3-OH 可以依次被所需的碳水化合物糖基化，生成生物所需的二糖。提出了一种涉及酸或碱辅助酰基迁移的机制。
• Sonochemistry:  A Powerful Way of Enhancing the Efficiency of Carbohydrate Synthesis
  作者：Shenglou Deng、Umesh Gangadharmath、Cheng-Wei Tom Chang

  DOI：10.1021/jo060374w

  日期：2006.7.1

  [GRAPHICS]Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation ( acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.
• Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains
  作者：Ichiro Matsuo、Megumi Isomura、Tatsuo Miyazaki、Tohru Sakakibara、Katsumi Ajisaka

  DOI：10.1016/s0008-6215(97)10001-5

  日期：1997.12

  Synthetic routes are described to a partial structure common to all high mannose-type sugar chains and complex-type sugar chains based on a chemoenzymatic strategy which incorporates, (a) enzymatic synthesis of oligosaccharide blocks using glycosidases, and (b) chemical synthesis of the branching oligosaccharides via regioselective coupling. All reaction products correspond to key intermediates necessary for the construction of N-linked oligosaccharides and we have synthesized the branched tetra-manno-oligosaccharide high mannose-type sugar chain and the branched hexa-oligosaccharide complex-type sugar chain using this simple and direct method. (C) 1998 Elsevier Science Ltd.