phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside | 460082-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside
• CAS: 460082-43-3
• 化学式: C₃₃H₃₂O₅S
• 分子量: 540.68
• InChiKey: QMAJDJRCTJQKFI-WGYVKSNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  11-hydroxytetradecanoic acid methyl ester 、 phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside 在 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到1-(methoxycarbonyl)tridec-10-yl 2-benzoyl-3,4-di-O-benzyl-6-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Preparation and diastereomeric separation of an (S)- and (R)-1-(methoxycarbonyl)tridec-10-yl glucoside derivative, a precursor for a monosaccharide constituent of resin glycosides

  摘要：

  The 6-O-mesyl derivative of phenyl 1-thio-beta-D-glucopyranoside was prepared from D-glucose as a synthetic equivalent of a 6-deoxy-hexosyl donor. Racemic methyl 11-hydroxytetradecanoate (methyl convolvulinolate) was synthesized by Grignard reaction of propylmagnesium bromide with 10-undecenal followed by hydroboration. Both intermediates were coupled by NIS-TfOH-promoted glycosidation to give a mixture of two diasteromeric glucopyranosides, which were separated on a preparative scale by medium pressure chromatography. One of the products was identified as having the natural (S)-configuration by comparison of its H-1 NMR spectrum with an authentic sample prepared from the corresponding chiral hydroxyfatty acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00092-7
• 作为产物：
  描述：

  phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 吡啶 、 sodium tetrahydroborate 、 二甲胺基甲硼烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Preparation and diastereomeric separation of an (S)- and (R)-1-(methoxycarbonyl)tridec-10-yl glucoside derivative, a precursor for a monosaccharide constituent of resin glycosides

  摘要：

  The 6-O-mesyl derivative of phenyl 1-thio-beta-D-glucopyranoside was prepared from D-glucose as a synthetic equivalent of a 6-deoxy-hexosyl donor. Racemic methyl 11-hydroxytetradecanoate (methyl convolvulinolate) was synthesized by Grignard reaction of propylmagnesium bromide with 10-undecenal followed by hydroboration. Both intermediates were coupled by NIS-TfOH-promoted glycosidation to give a mixture of two diasteromeric glucopyranosides, which were separated on a preparative scale by medium pressure chromatography. One of the products was identified as having the natural (S)-configuration by comparison of its H-1 NMR spectrum with an authentic sample prepared from the corresponding chiral hydroxyfatty acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00092-7