4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (1R)-S-oxide | 438587-70-3

• 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: 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (1R)-S-oxide
• 英文别名: 4-[(R)-[(1R,2R,5S,6S,7S)-6,7-dihydroxy-8-oxa-3-thiabicyclo[3.2.1]octan-2-yl]sulfinyl]benzonitrile
• CAS: 438587-70-3
• 化学式: C₁₃H₁₃NO₄S₂
• 分子量: 311.383
• InChiKey: CJOCVZNYQYTNGY-ZTHYODFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (1R)-S-oxide 以 吡啶 为溶剂， 反应 8.0h， 以82%的产率得到4-cyanophenyl 2,5-anhydro-3,4-di-O-(4-nitrobenzoyl)-1,6-dithio-α-D-glucoseptanoside (1R)-S-oxide
  参考文献：
  名称：

  The behavior of two thiosugar thioglycosides towards oxidation

  摘要：

  Oxidation of 4-cyanophenyl 2,5-anhydro-1,6-dithio-alpha-D-glucoseptanoside with magnesium monoperoxyphthalate (MMPP) resulted in a mixture containing two endo- and two exo-monosulfoxides as well as two endo-exo bis-sulfoxides differing in the chirality of the sulfoxide groups. Besides the aforementioned six products a further endo-exo bis-sulfoxide isomer as well as an exo-sulfone was obtained via oxidation with NaIO4. Oxidation of 4-nitrophenyl 1,5-dithio-beta-D-arabinopyranoside with MMPP yielded only two endo-sulfoxides, while oxidation with NaIO4 in turn led to cleavage of the carbohydrate ring. The formed dialdehyde was stabilized by cyclisation to a hemiacetall. which on further treatment with MMPP afforded an exo-monosulfoxide. The position of oxidation as well as the chirality of the respective sulfoxide groups was established by NMR spectroscopy and X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00034-4
• 作为产物：
  描述：

  4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以44%的产率得到4-cyanophenyl 2,5-anhydro-1,6-dithio-α-D-glucoseptanoside (6R)-S-oxide
  参考文献：
  名称：

  The behavior of two thiosugar thioglycosides towards oxidation

  摘要：

  Oxidation of 4-cyanophenyl 2,5-anhydro-1,6-dithio-alpha-D-glucoseptanoside with magnesium monoperoxyphthalate (MMPP) resulted in a mixture containing two endo- and two exo-monosulfoxides as well as two endo-exo bis-sulfoxides differing in the chirality of the sulfoxide groups. Besides the aforementioned six products a further endo-exo bis-sulfoxide isomer as well as an exo-sulfone was obtained via oxidation with NaIO4. Oxidation of 4-nitrophenyl 1,5-dithio-beta-D-arabinopyranoside with MMPP yielded only two endo-sulfoxides, while oxidation with NaIO4 in turn led to cleavage of the carbohydrate ring. The formed dialdehyde was stabilized by cyclisation to a hemiacetall. which on further treatment with MMPP afforded an exo-monosulfoxide. The position of oxidation as well as the chirality of the respective sulfoxide groups was established by NMR spectroscopy and X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00034-4

文献信息

• The behavior of two thiosugar thioglycosides towards oxidation
  作者：Éva Bozó、Ádám Demeter、Attila Rill、János Kuszmann

  DOI：10.1016/s0957-4166(02)00034-4

  日期：2002.1

  Oxidation of 4-cyanophenyl 2,5-anhydro-1,6-dithio-alpha-D-glucoseptanoside with magnesium monoperoxyphthalate (MMPP) resulted in a mixture containing two endo- and two exo-monosulfoxides as well as two endo-exo bis-sulfoxides differing in the chirality of the sulfoxide groups. Besides the aforementioned six products a further endo-exo bis-sulfoxide isomer as well as an exo-sulfone was obtained via oxidation with NaIO4. Oxidation of 4-nitrophenyl 1,5-dithio-beta-D-arabinopyranoside with MMPP yielded only two endo-sulfoxides, while oxidation with NaIO4 in turn led to cleavage of the carbohydrate ring. The formed dialdehyde was stabilized by cyclisation to a hemiacetall. which on further treatment with MMPP afforded an exo-monosulfoxide. The position of oxidation as well as the chirality of the respective sulfoxide groups was established by NMR spectroscopy and X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.