methyl [phenyl 9-O-t-butyl(diphenyl)silyl-5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate | 936346-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [phenyl 9-O-t-butyl(diphenyl)silyl-5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
• CAS: 936346-91-7
• 化学式: C₃₄H₄₃NO₈SSi
• 分子量: 653.869
• InChiKey: SHXAJTBJOUDESL-QGTHAJGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  134.55
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl [phenyl 9-O-t-butyl(diphenyl)silyl-5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 在 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 methyl [phenyl 5-acetamido-7,8-O-isopropylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
  参考文献：
  名称：

  Synthesis of Nor-C-linked Neuraminic Acid Disaccharide:  A Versatile Precursor of C-Analogs of Oligosialic Acids and Gangliosides

  摘要：

  The Neu5Ac alpha(2,8)Neu5Ac disaccharide is an important constituent of tumor related antigen, however, the O-linkage is catabolically unstable. Vaccination with a catabolically stable sialic acid C-glycoside analog might enhance immunogenicity. The synthesis of Neu5Ac nor-C-disaccharide 20R/S, corresponding to versatile precursors of C-analogs of oligosialic acid and gangliosides, is reported. The synthesis of the protected acceptor was not straightforward, as ester, silyl ether, and isopropylidene protection failed to afford desired C-linked disaccharide. Allyl ether protection of hydroxyl groups and acetyl protection of the acetamido facilitated the successful synthesis of the 8-aldehyde neuraminyl acceptor. Samarium mediated C-glycosylation afforded the desired nor-C-disaccharide as a mixture of two separable diastereomers.

  DOI：

  10.1021/jo0623787
• 作为产物：
  描述：

  methyl (phenyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galactonon-2-ulopyranoside)onate 、 叔丁基二苯基氯硅烷 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以50%的产率得到methyl [phenyl 9-O-t-butyl(diphenyl)silyl-5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
  参考文献：
  名称：

  Synthesis of Nor-C-linked Neuraminic Acid Disaccharide:  A Versatile Precursor of C-Analogs of Oligosialic Acids and Gangliosides

  摘要：

  The Neu5Ac alpha(2,8)Neu5Ac disaccharide is an important constituent of tumor related antigen, however, the O-linkage is catabolically unstable. Vaccination with a catabolically stable sialic acid C-glycoside analog might enhance immunogenicity. The synthesis of Neu5Ac nor-C-disaccharide 20R/S, corresponding to versatile precursors of C-analogs of oligosialic acid and gangliosides, is reported. The synthesis of the protected acceptor was not straightforward, as ester, silyl ether, and isopropylidene protection failed to afford desired C-linked disaccharide. Allyl ether protection of hydroxyl groups and acetyl protection of the acetamido facilitated the successful synthesis of the 8-aldehyde neuraminyl acceptor. Samarium mediated C-glycosylation afforded the desired nor-C-disaccharide as a mixture of two separable diastereomers.

  DOI：

  10.1021/jo0623787