(2S,3R,4R,5S)-2-((R)-1,2-Dihydroxy-ethyl)-5-(pyridin-2-ylsulfanyl)-tetrahydro-furan-3,4-diol | 514847-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S)-2-((R)-1,2-Dihydroxy-ethyl)-5-(pyridin-2-ylsulfanyl)-tetrahydro-furan-3,4-diol
• 英文别名: (2S,3R,4R,5S)-2-[(1R)-1,2-dihydroxyethyl]-5-pyridin-2-ylsulfanyloxolane-3,4-diol
• CAS: 514847-49-5
• 化学式: C₁₁H₁₅NO₅S
• 分子量: 273.31
• InChiKey: CICRQBGFYAOHJP-WJOQGRNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  辛醇 、 (2S,3R,4R,5S)-2-((R)-1,2-Dihydroxy-ethyl)-5-(pyridin-2-ylsulfanyl)-tetrahydro-furan-3,4-diol 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 n-octyl α-D-galactofuranoside 、 octyl β-D-galactofuranoside
  参考文献：
  名称：

  First O-Glycosylation from Unprotected 1-Thioimidoyl Hexofuranosides Assisted by Divalent Cations

  摘要：

  The preparation of O-hexofuranosides was accomplished from unprotected 1-thioimidoyl furanosides as donors. The present methodology was first used for the synthesis of octyl galactofuranoside and further extended to D-galactofuranose-containing disaccharides. Within this study, we emphasized the need for additional complexing cations to maintain the furanose ring in its initial size. After experimentation, calcium ion was first used concomitantly with trimethylsilyl trifluoromethanesulfonate, the latter being able to activate the thioimidate and the former being likely to inhibit ring expansion. Moreover, an improvement was performed by using copper(II) trifluoromethanesulfonate which could then meet the requirements as both promoter and complexing agent.

  DOI：

  10.1021/jo070741j
• 作为产物：
  描述：

  Acetic acid (2S,3S,4R,5S)-4-acetoxy-2-((R)-1,2-diacetoxy-ethyl)-5-(pyridin-2-ylsulfanyl)-tetrahydro-furan-3-yl ester 在 甲醇 、 sodium methylate 作用下， 以87%的产率得到(2S,3R,4R,5S)-2-((R)-1,2-Dihydroxy-ethyl)-5-(pyridin-2-ylsulfanyl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  A novel synthesis of d-galactofuranosyl, d-glucofuranosyl and d-mannofuranosyl 1-phosphates based on remote activation of new and free hexofuranosyl donors

  摘要：

  The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00822-3

文献信息

• A novel synthesis of d-galactofuranosyl, d-glucofuranosyl and d-mannofuranosyl 1-phosphates based on remote activation of new and free hexofuranosyl donors
  作者：Vincent Ferrières、Sophie Blanchard、Delphine Fischer、Daniel Plusquellec

  DOI：10.1016/s0960-894x(02)00822-3

  日期：2002.12

  The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series. (C) 2002 Elsevier Science Ltd. All rights reserved.
• First <i>O</i>-Glycosylation from Unprotected 1-Thioimidoyl Hexofuranosides Assisted by Divalent Cations
  作者：Ronan Euzen、Jean-Paul Guégan、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1021/jo070741j

  日期：2007.7.1

  The preparation of O-hexofuranosides was accomplished from unprotected 1-thioimidoyl furanosides as donors. The present methodology was first used for the synthesis of octyl galactofuranoside and further extended to D-galactofuranose-containing disaccharides. Within this study, we emphasized the need for additional complexing cations to maintain the furanose ring in its initial size. After experimentation, calcium ion was first used concomitantly with trimethylsilyl trifluoromethanesulfonate, the latter being able to activate the thioimidate and the former being likely to inhibit ring expansion. Moreover, an improvement was performed by using copper(II) trifluoromethanesulfonate which could then meet the requirements as both promoter and complexing agent.