(2S,4S,5R,6R)-4-Benzoyloxy-6-[(R)-benzoyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 192383-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-4-Benzoyloxy-6-[(R)-benzoyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 192383-15-6
• 化学式: C₂₈H₃₂O₁₁
• 分子量: 544.555
• InChiKey: LGUGBYUNSBOBMY-QYAXWPQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  136.05
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-4-Benzoyloxy-6-[(R)-benzoyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 四氧化钌 作用下， 以 四氯化碳 为溶剂， 以78%的产率得到(2S,4S,6S)-4-Benzoyloxy-6-[(R)-benzoyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-5-oxo-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Sialic Acid Analogues with the Oxime Group at C-4 Or C-5 of KDN¹

  摘要：

  The readily available methyl (methyl 3-deoxy-5,8:7, 9-di-O-isopropylidene-beta-D-glycero-D-galacto-2 -nonulopyranosid)onate (7) was converted in five synthetic steps into methyl (methyl 4-acetamido-3, 4-dideoxy-beta-D-glycero-D-talo-2-nonulopyranosid)onate (11). Selective protection of the C-4, C-7, C-8 and C-9 hydroxy groups of methyl (methyl 3-deoxy-8, 9-O-isopropylidene-beta-D-glycero-D-galacto-2 -nonulpyranosid)onate (2) followed by oxidation of the C-5 hydroxy group and then its oximination gave 5-hydroxyimino derivatives(l5 and 16).

  DOI：

  10.1080/07328309708007331
• 作为产物：
  描述：

  methyl (methyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate 在 吡啶 、 对甲苯磺酸 作用下， 反应 3.0h， 生成 (2S,4S,5R,6R)-4-Benzoyloxy-6-[(R)-benzoyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Sialic Acid Analogues with the Oxime Group at C-4 Or C-5 of KDN¹

  摘要：

  The readily available methyl (methyl 3-deoxy-5,8:7, 9-di-O-isopropylidene-beta-D-glycero-D-galacto-2 -nonulopyranosid)onate (7) was converted in five synthetic steps into methyl (methyl 4-acetamido-3, 4-dideoxy-beta-D-glycero-D-talo-2-nonulopyranosid)onate (11). Selective protection of the C-4, C-7, C-8 and C-9 hydroxy groups of methyl (methyl 3-deoxy-8, 9-O-isopropylidene-beta-D-glycero-D-galacto-2 -nonulpyranosid)onate (2) followed by oxidation of the C-5 hydroxy group and then its oximination gave 5-hydroxyimino derivatives(l5 and 16).

  DOI：

  10.1080/07328309708007331