phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-β-D-glucopyranoside | 237055-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-4-methyl-4-nitro-6-phenylsulfanyloxane-3,5-diol
• CAS: 237055-33-3
• 化学式: C₁₃H₁₇NO₆S
• 分子量: 315.347
• InChiKey: WIGKAQMXUYGRBB-BNDIWNMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-β-D-glucopyranoside 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以26%的产率得到phenyl 3,6-dideoxy-6-fluoro-3-C-methyl-3-nitro-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Branched-chain fluoro nitro d- and l-sugars from glucose

  摘要：

  sMixed crystals of methyl 3-deoxy-3-C-methyl-3-nitro-alpha-D- and beta-L-glucopyranosides (1:1), easily available from D-glucose by means of the Baer reaction, were completely characterised by X-ray diffraction analysis. These diastereomeric components, separation of which could be achieved through their 4,6-O-benzylidene derivatives, were selectively fluorinated at position 6 by treatment with DAST and stereoselectively transformed into phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-beta-D-glucopyranoside and phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-beta-L-glucopyranoside, respectively. Fluorination with DAST of each pure enantiomer afforded, depending on the conditions, the corresponding enantiomeric phenyl 3,6-dideoxy-6-fluoro-3-C-methyl-3-nitro-1-thio-beta-D- and beta-L-glucopyranosides or the respective rearranged 2,3,6-trideoxy-6-fluoro-3-C-methyl-3-nitro-2-alpha-D- and alpha-L-mannopyranosyl fluorides. This route constitutes a simple method for obtaining fair-to-good yields of 6-fluorinated branched-chain D- and L-sugar derivatives, potentially useful as glycosyl donors, starting from D-glucose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00156-1
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-3-nitro-α-D-glucopyranoside 在 吡啶 、 四丁基碘化铵 、 六甲基二硅氮烷 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Branched-chain fluoro nitro d- and l-sugars from glucose

  摘要：

  sMixed crystals of methyl 3-deoxy-3-C-methyl-3-nitro-alpha-D- and beta-L-glucopyranosides (1:1), easily available from D-glucose by means of the Baer reaction, were completely characterised by X-ray diffraction analysis. These diastereomeric components, separation of which could be achieved through their 4,6-O-benzylidene derivatives, were selectively fluorinated at position 6 by treatment with DAST and stereoselectively transformed into phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-beta-D-glucopyranoside and phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-beta-L-glucopyranoside, respectively. Fluorination with DAST of each pure enantiomer afforded, depending on the conditions, the corresponding enantiomeric phenyl 3,6-dideoxy-6-fluoro-3-C-methyl-3-nitro-1-thio-beta-D- and beta-L-glucopyranosides or the respective rearranged 2,3,6-trideoxy-6-fluoro-3-C-methyl-3-nitro-2-alpha-D- and alpha-L-mannopyranosyl fluorides. This route constitutes a simple method for obtaining fair-to-good yields of 6-fluorinated branched-chain D- and L-sugar derivatives, potentially useful as glycosyl donors, starting from D-glucose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00156-1

文献信息

• Branched-chain fluoro nitro d- and l-sugars from glucose
  作者：Ana T Carmona、Pastora Borrachero、Francisca Cabrera-Escribano、Mª Jesús Diánez、Mª Dolores Estrada、Amparo López-Castro、Rafael Ojeda、Manuel Gómez-Guillén、Simeón Pérez-Garrido

  DOI：10.1016/s0957-4166(99)00156-1

  日期：1999.5

  sMixed crystals of methyl 3-deoxy-3-C-methyl-3-nitro-alpha-D- and beta-L-glucopyranosides (1:1), easily available from D-glucose by means of the Baer reaction, were completely characterised by X-ray diffraction analysis. These diastereomeric components, separation of which could be achieved through their 4,6-O-benzylidene derivatives, were selectively fluorinated at position 6 by treatment with DAST and stereoselectively transformed into phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-beta-D-glucopyranoside and phenyl 3-deoxy-3-C-methyl-3-nitro-1-thio-beta-L-glucopyranoside, respectively. Fluorination with DAST of each pure enantiomer afforded, depending on the conditions, the corresponding enantiomeric phenyl 3,6-dideoxy-6-fluoro-3-C-methyl-3-nitro-1-thio-beta-D- and beta-L-glucopyranosides or the respective rearranged 2,3,6-trideoxy-6-fluoro-3-C-methyl-3-nitro-2-alpha-D- and alpha-L-mannopyranosyl fluorides. This route constitutes a simple method for obtaining fair-to-good yields of 6-fluorinated branched-chain D- and L-sugar derivatives, potentially useful as glycosyl donors, starting from D-glucose. (C) 1999 Elsevier Science Ltd. All rights reserved.