methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside | 83158-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside
• 英文别名: N-[(2S,3R,4R,6R)-3-hydroxy-6-methoxy-2,4-dimethyloxan-4-yl]acetamide
• CAS: 83158-18-3
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: QJRIHPJSWMGNKI-QRYDPKPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside 在 氨 、 calcium 、 间氯过氧苯甲酸 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 methyl 2,3,6-trideoxy-3-C-methyl-3-nitro-α-L-ribo-hexopyranoside
  参考文献：
  名称：

  The synthesis of a derivative of l-decilonitrose (2,3,6-trideoxy-3-C-methyl-3-nitro-l-ribo-hexose)

  摘要：

  DOI：

  10.1016/0008-6215(85)85062-x
• 作为产物：
  描述：

  methyl 3-acetamido-4-O-acetyl-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以80%的产率得到methyl 3-acetamido-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
• Synthetic Studies of the Cororubicin Oligosaccharide: Glycosylation of Branched Amino and Nitro Sugars
  作者：Lincoln Noecker、Franco Duarte、Robert M. Giuliano

  DOI：10.1080/07328309808005767

  日期：1998.1

  Derivatives of the branched amino sugar methyl 3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-ribo-hexopyranoside and its 3-nitro analog were coupled with glycosyl donors of 3,4-di-O-acetyl-2,6-dideoxy-L-fucopyranose. Successful glycosylations were developed using the fucosyl bromide, activated with silver triflate, and the fucosyl oxysilane, activated with trimethylsilyl triflate. High stereoselectivities for the desired alpha-1,4 linkage were observed in both cases. The N-trifluoroacetamido disaccharide was deacylated and the amino group oxidized to nitro with dimethyldioxirane. An alternate route based on coupling of the fucosyl bromide with the nitro sugar methyl alpha-L-decilonitroside also gave the a-linked disaccharide, which is related to oligosaccharides found in the antibiotics cororubicin and arugomycin.