phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside | 241490-69-7

• 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 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside
• 英文别名: [(2S,3R,4R,6R)-2,4-dimethyl-4-(phenylmethoxyamino)-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 241490-69-7
• 化学式: C₂₂H₂₇NO₄S
• 分子量: 401.527
• InChiKey: DMPYIMQLIZGXHW-HAFPXEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside 在 2,4,6-三甲基吡啶 、 (η(5)-cyclopentadienyl)zirconium dichloride radical 、 二乙胺基三氟化硫 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 二甲基二环氧乙烷 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 39.0h， 生成 methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1->4)-2,3,6-trideoxy-3-C-methyl-3-nitro-β-L-ribo-hexopyranosyl-(1->4)-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：

  O-benzyl phenyl-2,6-dideoxy-1-thio-α,β-erythro-hexopyranosid-3-ulose oxime 在 吡啶 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 反应 6.0h， 生成 phenyl 4-O-acetyl-3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-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