methyl 3-acetamido-4-O-acetyl-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside | 83212-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-acetamido-4-O-acetyl-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside
• CAS: 83212-40-2
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: YFDDHCIORRNZMO-FPQWWODTSA-N

物化性质

• 沸点：
  393.0±42.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-acetamido-4-O-acetyl-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside 在 盐酸 、 乙酸酐 作用下， 反应 24.0h， 以88 mg的产率得到2-methyl-5,6-dihydro-(4-O-acetyl-1,2,3,6-tetradeoxy-3-methyl-α-L-ribo-hexopyranoso)[3,2,1-de]-4H-1,3-oxazine
  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-C-cyano-2,6-dideoxy-4-O-methoxymethyl-3-O-methylsulphonyl-α-L-arabino-hexopyranoside 在 镍 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 氢气 作用下， 反应 1.5h， 生成 methyl 3-acetamido-4-O-acetyl-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside
  参考文献：
  名称：

  Brimacombe, John S.; Hanna, Roderick; Tucker, Leslie C.N., Journal of the Chemical Society. Perkin transactions I, 1983, # 10, p. 2277 - 2280

  摘要：

  DOI：

文献信息

• The synthesis of derivatives of 3-amino-2,3,6-trideoxy-3-C-methyl-l-xylo-hexopyranose, the novel branched-chain amino sugar of antibiotic A35512B
  作者：John S. Brimacombe、Roderick Hanna、Leslie C.N. Tucker

  DOI：10.1016/s0008-6215(00)81865-0

  日期：1982.7