methyl [phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3-(S)-3-²H-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate | 1606160-13-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl [phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3-(S)-3-²H-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate
• 英文别名: methyl (2S,3S,4S,5R,6R)-5-acetamido-4-acetyloxy-3-deuterio-2-phenylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 1606160-13-7
• 化学式: C₂₆H₃₃NO₁₂S
• 分子量: 584.606
• InChiKey: NPLKOUSSDBQHEN-ZQGCFWOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  195
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl [phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3-(S)-3-²H-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate 在 N-碘代丁二酰亚胺 、 甲烷磺酸 、 三氟甲磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 96.33h， 生成 methyl 4,7,8,9-tetra-O-acetyl-5-amino-2,6-anhydro-5,4-N,O-carbonyl-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate 、 methyl 4,7,8,9-tetra-O-acetyl-5-amino-2,6-anhydro-5,4-N,O-carbonyl-3,5-dideoxy-3-deuterio-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  Synthesis and Elimination of C-3-Labeled Thiosialosides

  摘要：

  The synthesis of C-3-labeled phenylthio sialic acid derivatives and an investigation of stereoselectivity in elimination reactions for the synthesis of 2,3-dehydro derivatives (glycals) is described. The experimental results are consistent with the existence of a conformational change and may be indicative of the intermediacy of an all-axial oxacarbenium ion.

  DOI：

  10.1021/ol500917k
• 作为产物：
  描述：

  methyl [5-acetamido-2,4,7,8,9-penta-O-acetyl-3-(S)-3-²H-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranos]onate 在 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 methyl [phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3-(S)-3-²H-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate
  参考文献：
  名称：

  Synthesis and Elimination of C-3-Labeled Thiosialosides

  摘要：

  The synthesis of C-3-labeled phenylthio sialic acid derivatives and an investigation of stereoselectivity in elimination reactions for the synthesis of 2,3-dehydro derivatives (glycals) is described. The experimental results are consistent with the existence of a conformational change and may be indicative of the intermediacy of an all-axial oxacarbenium ion.

  DOI：

  10.1021/ol500917k