(2R,4S,5R,6S)-4,5-Bis-benzoyloxy-6-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 192447-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6S)-4,5-Bis-benzoyloxy-6-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,4S,5R,6S)-4,5-dibenzoyloxy-6-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2-methoxyoxane-2-carboxylate
• CAS: 192447-83-9
• 化学式: C₂₈H₃₂O₁₁
• 分子量: 544.555
• InChiKey: UORREJPUBNZFQY-GKVARPHVSA-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：

  (2R,4S,5R,6S)-4,5-Bis-benzoyloxy-6-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-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， 反应 48.0h， 以52%的产率得到(2R,4S)-4-Benzoyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolane-4-carbonyl)-2-methoxy-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Oxidation Products of C-4 and C-7 Hydroxyls in the Methyl α-Glycoside Derivatives of KDN¹

  摘要：

  A regioselective protection of hydroxyl groups in the methyl ester-methyl alpha-glycoside derivative of KDN was demonstrated. Isopropylidenation of methyl (methyl 3-deoxy-alpha-D-glycero-D-galacto-2-nonulopyranosid)onate (1) gave mono- (8,9) and di- (5,7:8,9) O-isopropylidene derivatives. Benzoylation of methyl (methyl 3-deoxy-8, 9-O-isopropylidene-alpha-D-glycero-D-galacto-2 -nonulopyranosid)onate (7) gave di- (4,5) and tri- (4,5,7) O-benzoates. Through these reactions, it was found that the reactivity of the hydroxyl groups was different from that of methyl beta-glycoside of KDN. Oxidation products of C-4 and C-7 hydroxyl groups (6 and 11) were synthesized from these compounds.

  DOI：

  10.1080/07328309708007332
• 作为产物：
  描述：

  methyl (methyl 3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 32.0h， 生成 (2R,4S,5R,6S)-4,5-Bis-benzoyloxy-6-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Oxidation Products of C-4 and C-7 Hydroxyls in the Methyl α-Glycoside Derivatives of KDN¹

  摘要：

  A regioselective protection of hydroxyl groups in the methyl ester-methyl alpha-glycoside derivative of KDN was demonstrated. Isopropylidenation of methyl (methyl 3-deoxy-alpha-D-glycero-D-galacto-2-nonulopyranosid)onate (1) gave mono- (8,9) and di- (5,7:8,9) O-isopropylidene derivatives. Benzoylation of methyl (methyl 3-deoxy-8, 9-O-isopropylidene-alpha-D-glycero-D-galacto-2 -nonulopyranosid)onate (7) gave di- (4,5) and tri- (4,5,7) O-benzoates. Through these reactions, it was found that the reactivity of the hydroxyl groups was different from that of methyl beta-glycoside of KDN. Oxidation products of C-4 and C-7 hydroxyl groups (6 and 11) were synthesized from these compounds.

  DOI：

  10.1080/07328309708007332