(2S,3S,4S,6S)-6-((2S,3R,4R,6R)-4-Amino-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3,4-diol | 203176-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,6S)-6-((2S,3R,4R,6R)-4-Amino-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3,4-diol
• 英文别名: (2S,3S,4S,6S)-6-[(2S,3R,4R,6R)-4-amino-6-methoxy-2,4-dimethyloxan-3-yl]oxy-2-methyloxane-3,4-diol
• CAS: 203176-54-9
• 化学式: C₁₄H₂₇NO₆
• 分子量: 305.371
• InChiKey: VFMUEJJPWPYBCX-JWMVDTHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,6S)-6-((2S,3R,4R,6R)-4-Amino-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3,4-diol 在 Oxone 、 碳酸氢钠 、 臭氧 作用下， 以 水 、 丙酮 为溶剂， 反应 2.5h， 以85%的产率得到(2S,3S,4S,6S)-6-((2S,3R,4R,6R)-6-Methoxy-2,4-dimethyl-4-nitro-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  臭氧/氧酮介导的氨基酸和邻-苄基羟肟基糖的氧化

  摘要：

  描述了通过用混合氧化剂氧化由相应的氨基糖制备C-甲基支链硝基糖的方法。在OXONE（单过硫酸钾）和丙酮（Bashir-Hashemi法）存在下，对氨基糖进行臭氧分解可以得到高收率的硝化糖。通过该方法氧化O-苄基羟氨基糖导致脱保护和一步氧化，直接得到硝基糖。与DMDO相比，混合氧化剂方法在实验上更简单，更方便使用，而DMDO先前已被报道用于氨基糖的氧化。

  DOI：

  10.1081/car-120016852
• 作为产物：
  描述：

  methyl 3-amino-2,3,6-trideoxy-3-C-methyl-α-L-ribo-hexopyranoside 在 2,4,6-三甲基吡啶 、 lithium hydroxide 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 6.5h， 生成 (2S,3S,4S,6S)-6-((2S,3R,4R,6R)-4-Amino-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Synthetic Studies of the Cororubicin Oligosaccharide: Glycosylation of Branched Amino and Nitro Sugars

  摘要：

  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.

  DOI：

  10.1080/07328309808005767