(S)-1-(methoxycarbonyl)tridec-10-yl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-1-(methoxycarbonyl)tridec-10-yl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-2-[(4S)-14-methoxy-14-oxotetradecan-4-yl]oxy-6-(methylsulfonyloxymethyl)-4,5-bis(phenylmethoxy)oxan-3-yl] benzoate
• 化学式: C₄₃H₅₈O₁₁S
• 分子量: 782.993
• InChiKey: SXTAHAMHQSYGSD-QBWSQDNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  55
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  10-十一烯醛 在 sodium chlorite 、 N-氯代丁二酰亚胺 、 N-碘代丁二酰亚胺 、 2,2,6,6-四甲基哌啶氧化物 、 三氟甲磺酸 、 4 Angstroem MS 、 硼烷 、 四丁基氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 7.33h， 生成 (S)-1-(methoxycarbonyl)tridec-10-yl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-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

文献信息

• 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
  作者：Shigeru Kobayashi、Jun-ichi Furukawa、Tomoko Sakai、Nobuo Sakairi

  DOI：10.1016/s0008-6215(02)00092-7

  日期：2002.6

  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.