phenyl-3,4,6-tri-O-benzyl-1-seleno-α-D-galactopyranoside | 1228930-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl-3,4,6-tri-O-benzyl-1-seleno-α-D-galactopyranoside
• 英文别名: (2R,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylselanyloxan-3-ol
• CAS: 1228930-07-1
• 化学式: C₃₃H₃₄O₅Se
• 分子量: 589.59
• InChiKey: VCDIZJLUSYCNEO-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯硒酚 、 1,2-anhydro-3,4,6-tri-O-benzyl-D-galactopyranose 在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到phenyl-3,4,6-tri-O-benzyl-1-seleno-α-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of β-Phenylselenoglycosides from Glycals and Rationalization of the Selenoglycosylation Processes

  摘要：

  beta-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe(-)) with glycals. A rationalization of the presently described beta-selectivity and the opposite alpha-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.

  DOI：

  10.1021/jo100145s

文献信息

• Stereoretentive Reactions at the Anomeric Position: Synthesis of Selenoglycosides
  作者：Feng Zhu、Sloane O'Neill、Jacob Rodriguez、Maciej A. Walczak

  DOI：10.1002/anie.201802847

  日期：2018.6.11

  Reported is the stereospecific cross‐coupling of anomeric stannanes with symmetrical diselenides, resulting in the synthesis of selenoglycosides with exclusive anomeric control. The reaction proceeds without the need for directing groups and is compatible with free hydroxy groups as demonstrated in the preparation of glycoconjugates derived from mono‐, di‐, and trisaccharides and peptides (35 examples)

  报道了异头锡烷与对称二硒化物的立体特异性交叉偶联，从而合成了具有独家异头控制的硒糖苷。该反应无需定向基团即可进行，并且与游离羟基相容，如从单糖、二糖和三糖和肽衍生的糖缀合物的制备中所证明的（35 个示例）。鉴于其普遍性和广泛的底物范围，本文介绍的糖基交叉偶联方法可用于合成含硒糖模拟物和糖缀合物。
• Stereoselective Synthesis of β-Phenylselenoglycosides from Glycals and Rationalization of the Selenoglycosylation Processes
  作者：Valeria Di Bussolo、Annalisa Fiasella、Federica Balzano、Gloria Uccello Barretta、Paolo Crotti

  DOI：10.1021/jo100145s

  日期：2010.6.18

  beta-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe(-)) with glycals. A rationalization of the presently described beta-selectivity and the opposite alpha-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.