phenyl 2-azido-2-deoxy-6-O-(tert-butyl-dimethyl-silyl)-1-seleno-α-D-galactopyranoside | 282736-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-azido-2-deoxy-6-O-(tert-butyl-dimethyl-silyl)-1-seleno-α-D-galactopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-5-azido-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-phenylselanyloxane-3,4-diol
• CAS: 282736-07-6
• 化学式: C₁₈H₂₉N₃O₄SeSi
• 分子量: 458.491
• InChiKey: XRISVLYIRIHGCL-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  73.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2-azido-2-deoxy-6-O-(tert-butyl-dimethyl-silyl)-1-seleno-α-D-galactopyranoside 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of a Tetrasaccharide Glycosyl Glycerol. Precursor to Glycolipids of Meiothermus taiwanensis ATCC BAA-400

  摘要：

  Synthesis of a tetrasaccharide glycosyl glycerol, the core structure of glycoglycerolipid from Meiothermus taiwanensis ATCC BAA-400, was described. A one-pot glycosylation with three components was employed as a key step.

  DOI：

  10.1021/jo070629l
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 phenyl 2-azido-2-deoxy-1-seleno-α-D-galactopyranoside 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以93.8%的产率得到phenyl 2-azido-2-deoxy-6-O-(tert-butyl-dimethyl-silyl)-1-seleno-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Tetrasaccharide Glycosyl Glycerol. Precursor to Glycolipids of Meiothermus taiwanensis ATCC BAA-400

  摘要：

  Synthesis of a tetrasaccharide glycosyl glycerol, the core structure of glycoglycerolipid from Meiothermus taiwanensis ATCC BAA-400, was described. A one-pot glycosylation with three components was employed as a key step.

  DOI：

  10.1021/jo070629l

文献信息

• A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor
  作者：Weir-Torn Jiaang、Meng-Yang Chang、Ping-Hui Tseng、Shui-Tein Chen

  DOI：10.1016/s0040-4039(00)00367-1

  日期：2000.4

  A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yield with high alpha selectivity. From protected D-galactal, a protected TF antigen building block is obtained in 40% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.