methyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-β-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside | 241490-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-β-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside
• 英文别名: [(2S,3R,4R,6R)-6-[(2S,3R,4S,6R)-6-methoxy-2-methyl-4-phenylmethoxyoxan-3-yl]oxy-2,4-dimethyl-4-(phenylmethoxyamino)oxan-3-yl] acetate
• CAS: 241490-72-2
• 化学式: C₃₀H₄₁NO₈
• 分子量: 543.657
• InChiKey: HRERKKWPVUPDRV-RYMPFVOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-β-L-ribo-hexopyranosyl-(1->4)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranoside 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 15.0h， 生成 methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1->4)-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-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：

  phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside 在 (η(5)-cyclopentadienyl)zirconium dichloride radical 、 二乙胺基三氟化硫 、 silver trifluoromethanesulfonate 作用下， 生成 methyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-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

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.