(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

文献信息

• 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.
• OZONE/OXONE-MEDIATED OXIDATIONS OF AMINO AND O-BENZYLHYDROXYLAMINO SUGARS
  作者：Lincoln Noecker、Robert Giuliano、Michael Cooney、Walter Boyko、Walter Zajac, Jr.

  DOI：10.1081/car-120016852

  日期：——

  A method for the preparation of C-methyl branched nitro sugars from the corresponding amino sugars by oxidation with mixed oxidants is described. Ozonolysis of the amino sugars in the presence of OXONE (potassium monopersulfate) and acetone (Bashir-Hashemi's procedure) gave nitro sugars in good yields. Oxidation of an O-benzylhydroxylamino sugar by this method resulted in deprotection and oxidation

  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。