2,2,2-Trifluoro-N-((2S,3R,4R,6R)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-acetamide | 203176-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trifluoro-N-((2S,3R,4R,6R)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-acetamide
• 英文别名: 2,2,2-trifluoro-N-[(2S,3R,4R,6R)-3-hydroxy-6-methoxy-2,4-dimethyloxan-4-yl]acetamide
• CAS: 203176-45-8
• 化学式: C₁₀H₁₆F₃NO₄
• 分子量: 271.237
• InChiKey: UUQVDNNJJUCRNH-VOQBNFLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluoro-N-((2S,3R,4R,6R)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-acetamide 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 phenyl 4-O-acetyl-2,3,6-trideoxy-3-C-methyl-3-(O-trifluoroacetamido)-1-thio-α-L-ribo-hexopyranoside
  参考文献：
  名称：

  Glycosylation of Branched Amino and Nitro Sugars. 2. Synthesis of the Cororubicin Trisaccharide

  摘要：

  The synthesis of the nitro-sugar-containing trisaccharide found in the antibiotic cororubicin is described. This trisaccharide contains the nitro sugar L-decilonitrose which is attached to two digitoxose residues (a dideoxy sugar) by beta-1,4 and alpha-1,4 linkages. The target trisaccharide synthesized was methyl 2,6-dideoxy-alpha-L-lyxo-hexopyranosyl-(1-->4)-2,3,6-trideoxy-3-C-methyl-3-nitro-beta-L-ribo-hexopyranosyl-( 1-->4)-2,6-dideoxy-alpha-L-lyxo-hexopyranoside The principle features of the synthesis are the use of an O-benzylhydroxylamino sugar as the precursor to the nitro sugar decilonitrose and as both the acceptor and donor in glycosyations, a beta-selective glycosylation by means of a thioglycoside donor, and novel functional group transformations carried out on the assembled trisaccharide. These include oxidative cleavage of the O-benzylhydroxylamino group to nitro, carried out with dimethyldioxirane in one step. This transformation proved critical in completing the synthesis, which is the first reported of one of the decilonitrose-containing trisaccharides found in antibiotics.

  DOI：

  10.1021/jo990403l
• 作为产物：
  描述：

  methyl 3-amino-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside 、 三氟乙酸酐 以 二氯甲烷 为溶剂， 反应 2.5h， 以91%的产率得到2,2,2-Trifluoro-N-((2S,3R,4R,6R)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-acetamide
  参考文献：
  名称：

  Synthetic Studies of the Cororubicin Oligosaccharide: Glycosylation of Branched Amino and Nitro Sugars

  摘要：

  Derivatives of the branched amino sugar methyl 3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-ribo-hexopyranoside and its 3-nitro analog were coupled with glycosyl donors of 3,4-di-O-acetyl-2,6-dideoxy-L-fucopyranose. Successful glycosylations were developed using the fucosyl bromide, activated with silver triflate, and the fucosyl oxysilane, activated with trimethylsilyl triflate. High stereoselectivities for the desired alpha-1,4 linkage were observed in both cases. The N-trifluoroacetamido disaccharide was deacylated and the amino group oxidized to nitro with dimethyldioxirane. An alternate route based on coupling of the fucosyl bromide with the nitro sugar methyl alpha-L-decilonitroside also gave the a-linked disaccharide, which is related to oligosaccharides found in the antibiotics cororubicin and arugomycin.

  DOI：

  10.1080/07328309808005767

文献信息

• Glycosylation of Branched Amino and Nitro Sugars. 2. Synthesis of the Cororubicin Trisaccharide
  作者：Lincoln Noecker、Franco Duarte、Scott A. Bolton、Wayne G. McMahon、Maria T. Diaz、Robert M. Giuliano

  DOI：10.1021/jo990403l

  日期：1999.8.1

  The synthesis of the nitro-sugar-containing trisaccharide found in the antibiotic cororubicin is described. This trisaccharide contains the nitro sugar L-decilonitrose which is attached to two digitoxose residues (a dideoxy sugar) by beta-1,4 and alpha-1,4 linkages. The target trisaccharide synthesized was methyl 2,6-dideoxy-alpha-L-lyxo-hexopyranosyl-(1-->4)-2,3,6-trideoxy-3-C-methyl-3-nitro-beta-L-ribo-hexopyranosyl-( 1-->4)-2,6-dideoxy-alpha-L-lyxo-hexopyranoside The principle features of the synthesis are the use of an O-benzylhydroxylamino sugar as the precursor to the nitro sugar decilonitrose and as both the acceptor and donor in glycosyations, a beta-selective glycosylation by means of a thioglycoside donor, and novel functional group transformations carried out on the assembled trisaccharide. These include oxidative cleavage of the O-benzylhydroxylamino group to nitro, carried out with dimethyldioxirane in one step. This transformation proved critical in completing the synthesis, which is the first reported of one of the decilonitrose-containing trisaccharides found in antibiotics.
• Synthetic Studies of the Cororubicin Oligosaccharide: Glycosylation of Branched Amino and Nitro Sugars
  作者：Lincoln Noecker、Franco Duarte、Robert M. Giuliano

  DOI：10.1080/07328309808005767

  日期：1998.1

  Derivatives of the branched amino sugar methyl 3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-ribo-hexopyranoside and its 3-nitro analog were coupled with glycosyl donors of 3,4-di-O-acetyl-2,6-dideoxy-L-fucopyranose. Successful glycosylations were developed using the fucosyl bromide, activated with silver triflate, and the fucosyl oxysilane, activated with trimethylsilyl triflate. High stereoselectivities for the desired alpha-1,4 linkage were observed in both cases. The N-trifluoroacetamido disaccharide was deacylated and the amino group oxidized to nitro with dimethyldioxirane. An alternate route based on coupling of the fucosyl bromide with the nitro sugar methyl alpha-L-decilonitroside also gave the a-linked disaccharide, which is related to oligosaccharides found in the antibiotics cororubicin and arugomycin.