phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside | 241490-66-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside
• 英文别名: 3-(O-benzylhydroxylamine)-1-thiophenol-L-saccharosamine；(2S,3R,4R,6S)-2,4-dimethyl-4-(phenylmethoxyamino)-6-phenylsulfanyloxan-3-ol
• CAS: 241490-66-4
• 化学式: C₂₀H₂₅NO₃S
• 分子量: 359.489
• InChiKey: AFLQZDBSEGVJOJ-MVJPYGJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside 在 吡啶 、 (η(5)-cyclopentadienyl)zirconium dichloride radical 、 二乙胺基三氟化硫 、 silver trifluoromethanesulfonate 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 methyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-α-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：

  甲基锂 、 O-benzyl phenyl-2,6-dideoxy-1-thio-α,β-erythro-hexopyranosid-3-ulose oxime 在 cerium(III) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以42%的产率得到phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-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

文献信息

• Rapid <i>de Novo</i> Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization
  作者：Subbarao Yalamanchili、William Miller、Xizhao Chen、Clay S. Bennett

  DOI：10.1021/acs.orglett.9b03812

  日期：2019.12.6

  A flexible de novo route capable of producing libraries of 2,6-dideoxy sugars is described. We have found that Au(JackiePhos)SbF6MeCN promotes the conversion of homopropargyl orthoesters into functionalized 2,3-dihydro-4H-pyran-4-ones in good to excellent yields (71-90%). These latter compounds can be easily converted into a number of otherwise difficult to access 2,6-dideoxy sugars.

  描述了一种能够产生 2,6-二脱氧糖文库的灵活的从头路线。我们发现 Au(JackiePhos)SbF6MeCN 可以促进均炔丙基原酸酯转化为功能化 2,3-二氢-4H-吡喃-4-酮，产率从良好到优异 (71-90%)。后面这些化合物可以很容易地转化为许多原本难以获得的 2,6-二脱氧糖。
• 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.