1-(S)-ethylsulfinyl-3,4,6-tri-O-pivaloyl-1,2-dideoxy-2-amino-β-D-glucopyranoside | 502507-89-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(S)-ethylsulfinyl-3,4,6-tri-O-pivaloyl-1,2-dideoxy-2-amino-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-amino-3,4-bis(2,2-dimethylpropanoyloxy)-6-[(S)-ethylsulfinyl]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 502507-89-3
• 化学式: C₂₃H₄₁NO₈S
• 分子量: 491.646
• InChiKey: OCCIHIIFMMZKTM-LRJCWXKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯甲醛 、 1-(S)-ethylsulfinyl-3,4,6-tri-O-pivaloyl-1,2-dideoxy-2-amino-β-D-glucopyranoside 在 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以71%的产率得到1-(S)-ethylsulfinyl-1,2-dideoxy-2-p-methoxybenzylideneamino-3,4,6-tri-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Highly Diastereoselective Oxidation of 2-Amino-2-deoxy-1-thio-β-d-glucopyranosides:  Synthesis of Imino Sulfinylglycosides

  摘要：

  A synthetic route to imino thioglycosides and to imino sulfinylglycosides has been developed. A detailed study on the diastereoselective oxidation of 2-amino-2-deoxy-1-thio-beta-D-glucopyranosides is reported. It has been shown that the stereochemical outcome of the oxidation is highly dependent on the protective group of the amine function. While the oxidation of iminothioglycosides is slightly diastereoselective (up to 30% de in favor of the R-S sulfoxide), a single isomer is obtained in the case of tetrachloroplithalimido derivatives. The absolute configuration of the sulfinyl glycoside was ascertained by NMR analysis using our recent model on the basis of the exo-anomeric effect corroborated by X-ray crystallography.

  DOI：

  10.1021/jo026519q
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-α-D-glucopyranoside 在 盐酸 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 水 、 乙二胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 65.25h， 生成 1-(S)-ethylsulfinyl-3,4,6-tri-O-pivaloyl-1,2-dideoxy-2-amino-β-D-glucopyranoside
  参考文献：
  名称：

  Highly Diastereoselective Oxidation of 2-Amino-2-deoxy-1-thio-β-d-glucopyranosides:  Synthesis of Imino Sulfinylglycosides

  摘要：

  A synthetic route to imino thioglycosides and to imino sulfinylglycosides has been developed. A detailed study on the diastereoselective oxidation of 2-amino-2-deoxy-1-thio-beta-D-glucopyranosides is reported. It has been shown that the stereochemical outcome of the oxidation is highly dependent on the protective group of the amine function. While the oxidation of iminothioglycosides is slightly diastereoselective (up to 30% de in favor of the R-S sulfoxide), a single isomer is obtained in the case of tetrachloroplithalimido derivatives. The absolute configuration of the sulfinyl glycoside was ascertained by NMR analysis using our recent model on the basis of the exo-anomeric effect corroborated by X-ray crystallography.

  DOI：

  10.1021/jo026519q

文献信息

• Highly Diastereoselective Oxidation of 2-Amino-2-deoxy-1-thio-β-<scp>d</scp>-glucopyranosides:  Synthesis of Imino Sulfinylglycosides
  作者：Noureddine Khiar、Inmaculada Fernández、Cristina S. Araújo、José-Antonio Rodríguez、Belén Suárez、Eleuterio Álvarez

  DOI：10.1021/jo026519q

  日期：2003.2.1

  A synthetic route to imino thioglycosides and to imino sulfinylglycosides has been developed. A detailed study on the diastereoselective oxidation of 2-amino-2-deoxy-1-thio-beta-D-glucopyranosides is reported. It has been shown that the stereochemical outcome of the oxidation is highly dependent on the protective group of the amine function. While the oxidation of iminothioglycosides is slightly diastereoselective (up to 30% de in favor of the R-S sulfoxide), a single isomer is obtained in the case of tetrachloroplithalimido derivatives. The absolute configuration of the sulfinyl glycoside was ascertained by NMR analysis using our recent model on the basis of the exo-anomeric effect corroborated by X-ray crystallography.