[(2S,3R,4R,6S)-6-fluoro-2,4-dimethyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] acetate | 1053729-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [(2S,3R,4R,6S)-6-fluoro-2,4-dimethyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] acetate
• CAS: 1053729-02-4
• 化学式: C₁₁H₁₅F₄NO₄
• 分子量: 301.238
• InChiKey: WONJVILPRZIPBY-LHGNLISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside 、 [(2S,3R,4R,6S)-6-fluoro-2,4-dimethyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] acetate 在 (η(5)-cyclopentadienyl)zirconium dichloride radical 、 silver trifluoromethanesulfonate 作用下， 生成 methyl 4-O-acetyl-2,3,6-trideoxy-3-C-methyl-3-(trifluoroacetamido)-α-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside 、 methyl 4-O-acetyl-2,3,6-trideoxy-3-C-methyl-3-(trifluoroacetamido)-β-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-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：

  2,2,2-Trifluoro-N-((2S,3R,4R,6R)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-acetamide 在 二乙胺基三氟化硫 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S,3R,4R,6S)-6-fluoro-2,4-dimethyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] acetate
  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