(2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-2-phenylsulfanyl-6-trimethylsilanyloxymethyl-tetrahydro-pyran-4-ol | 675876-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-2-phenylsulfanyl-6-trimethylsilanyloxymethyl-tetrahydro-pyran-4-ol
• 英文别名: (2S,3R,4R,5R,6R)-3-azido-5-phenylmethoxy-2-phenylsulfanyl-6-(trimethylsilyloxymethyl)oxan-4-ol
• CAS: 675876-43-4
• 化学式: C₂₂H₂₉N₃O₄SSi
• 分子量: 459.641
• InChiKey: DPZZNUDBFPWSRX-YXIAPDDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-2-phenylsulfanyl-6-trimethylsilanyloxymethyl-tetrahydro-pyran-4-ol 在 二氯二茂锆 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach

  摘要：

  We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl anther. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.042
• 作为产物：
  描述：

  phenyl 1-thio-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 咪唑 、 硼烷四氢呋喃络合物 、 三氟甲磺酸二丁硼 、 氢氟酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-2-phenylsulfanyl-6-trimethylsilanyloxymethyl-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach

  摘要：

  We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl anther. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.042

文献信息

• Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach
  作者：Hiroshi Tanaka、Masaatsu Adachi、Takashi Takahashi

  DOI：10.1016/j.tetlet.2003.12.042

  日期：2004.2

  We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl anther. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields. (C) 2003 Elsevier Ltd. All rights reserved.