methyl 3-azido-3-deoxy-2-O-(p-tolylsulfonyl)-β-D-xylofuranoside | 175655-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-azido-3-deoxy-2-O-(p-tolylsulfonyl)-β-D-xylofuranoside
• 英文别名: methyl 3-azido-O²-(toluene-4-sulfonyl)-β-D-3-deoxy-xylofuranoside；Methyl-<3-azido-O²-(toluol-4-sulfonyl)-3-desoxy-β-D-xylofuranosid>；Methyl-3-azido-deoxy-2-O-p-tolylsulfonyl-β-D-xylofuranosid；[(2R,3R,4S,5S)-4-azido-5-(hydroxymethyl)-2-methoxyoxolan-3-yl] 4-methylbenzenesulfonate
• CAS: 175655-96-6
• 化学式: C₁₃H₁₇N₃O₆S
• 分子量: 343.36
• InChiKey: QOJKXCVFOWHGCJ-YVECIDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-3-deoxy-2-O-(p-tolylsulfonyl)-β-D-xylofuranoside 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 4.5h， 以91%的产率得到(2S,3S,4R,5R)-3-azido-5-methoxy-4-(4-methylphenyl)sulfonyloxyoxolane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Optically Pure 3,4-Disubstituted l-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative

  摘要：

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.

  DOI：

  10.1021/jo951983z
• 作为产物：
  描述：

  methyl 5-O-trityl-β-D-ribofuranoside 在 吡啶 、 氯化亚砜 、 sodium azide 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 六甲基磷酰三胺 为溶剂， 反应 89.25h， 生成 methyl 3-azido-3-deoxy-2-O-(p-tolylsulfonyl)-β-D-xylofuranoside
  参考文献：
  名称：

  Synthesis of Optically Pure 3,4-Disubstituted l-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative

  摘要：

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.

  DOI：

  10.1021/jo951983z

文献信息

• Synthesis of some N-substituted methyl 2,3-dideoxy-2,3-epimino-β-<scp>D</scp>-lyxofuranosides
  作者：J. Cleophax、S. D. Gero、J. Hildesheim、A. M. Sepulchre、R. D. Guthrie、C. W. Smith

  DOI：10.1039/j39700001385

  日期：——

  Several N-substituted methyl 2,3-dideoxy-2,3-epimino-β-D-lyxofuranosides are described, including compounds in the 5-deoxy-series. In most cases, the epimines were synthesized from the appropriate 3-azido-3-deoxy-2-p-tolysulphonyloxy-xylo-derivatives, which in turn were prepared from the 2,3-bis-p- tolysulphonyloxy-ribo-compounds. The azidolysis of methyl 2,3-N-benzoylepimino-2,3-dideoxy-β-D-lyxofuranoside is described.

  本文介绍了几种 N-取代甲基 2,3-二脱氧-2,3-表亚胺-δ²-D-来苏呋喃糖苷，包括 5-脱氧系列的化合物。在大多数情况下，表亚胺是由适当的 3-叠氮-3-脱氧-2-对甲苯磺酰氧基氧基衍生物合成的，而后者又是由 2,3-双对甲苯磺酰氧基核化合物制备的。介绍了甲基 2,3-N-苯甲酰基吡喃-2,3-二脱氧-δ-²-D-来苏呋喃糖苷的叠氮分解。
• Synthesis of Optically Pure 3,4-Disubstituted <scp>l</scp>-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative
  作者：Philippe Dauban、Angèle Chiaroni、Claude Riche、Robert H. Dodd

  DOI：10.1021/jo951983z

  日期：1996.1.1

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.