methyl [phenyl 5-acetamido-9-O-(p-methoxy)benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate | 936346-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [phenyl 5-acetamido-9-O-(p-methoxy)benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-[(4-methoxyphenyl)methoxy]propyl]-4-hydroxy-2-phenylsulfanyloxane-2-carboxylate
• CAS: 936346-94-0
• 化学式: C₂₆H₃₃NO₉S
• 分子量: 535.615
• InChiKey: CWHMMZGLUUPKAE-UQJVNAJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl [phenyl 5-acetamido-9-O-(p-methoxy)benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 在 barium hydroxide octahydrate 、 ammonium cerium(IV) nitrate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 barium(II) oxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.5h， 生成 allyl [phenyl 4,7,8-tri-O-allyl-5-(N-acetylacetamido)-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-(9-oxa-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-8,9-O-(p-methoxy)benzylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 在 三氯化铝 、 硼烷-三甲胺络合物 作用下， 以 四氢呋喃 为溶剂， 以52.7%的产率得到methyl [phenyl 5-acetamido-9-O-(p-methoxy)benzyl-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

文献信息

• Stereoselective Synthesis of a <i>C</i>-Linked Neuraminic Acid Disaccharide: Potential Building Block for the Synthesis of <i>C</i>-Analogues of Polysialic acids
  作者：Jin-Hwan Kim、Fei Huang、Mellisa Ly、Robert J. Linhardt

  DOI：10.1021/jo801946y

  日期：2008.12.5

  C-Linked neuraminic acid disaccharide was synthesized in a diastereoselective manner from a sulfone donor and aldehyde acceptor, which was protected as a propargyl ether, through a samarium-mediated coupling reaction. The resulting disaccharide has acetal and phenyl sulfide functional C groups that can be easily converted into aldehyde and phenyl sulfone groups by photolysis and oxidation reactions to serve as disaccharide acceptor and donor, respectively.
• Synthesis of Nor-<i>C</i>-linked Neuraminic Acid Disaccharide:  A Versatile Precursor of <i>C</i>-Analogs of Oligosialic Acids and Gangliosides
  作者：Xuejun Yuan、Dino K. Ress、Robert J. Linhardt

  DOI：10.1021/jo0623787

  日期：2007.4.1

  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.