methyl [phenyl 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(S)-deuterio-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate | 1606160-24-0

• 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 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(S)-deuterio-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate
• 英文别名: methyl (3aR,4R,6S,7S,7aS)-7-deuterio-2-oxo-6-phenylsulfanyl-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydro-3H-pyrano[3,4-d][1,3]oxazole-6-carboxylate
• CAS: 1606160-24-0
• 化学式: C₂₃H₂₇NO₁₁S
• 分子量: 526.526
• InChiKey: JQQNTEZKESNNRX-BTAWBYNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl [phenyl 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(S)-deuterio-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside]onate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 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：

  在 甲烷磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 112.0h， 生成 methyl [phenyl 7,8,9-tri-O-acetyl-5-amino-5,4-N,O-carbonyl-3-(S)-deuterio-3,5-dideoxy-2-thio-D-glycero-α-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