(4R,4aR,6R,8S,8aR)-8-Acetoxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester | 192447-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,4aR,6R,8S,8aR)-8-Acetoxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester
• 英文别名: methyl (4R,4aR,6R,8S,8aR)-8-acetyloxy-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methoxy-2,2-dimethyl-4a,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxine-6-carboxylate
• CAS: 192447-77-1
• 化学式: C₁₉H₃₀O₁₀
• 分子量: 418.441
• InChiKey: WZJLOSPVUJETDL-XKXHLLLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4R,4aR,6R,8S,8aR)-8-Acetoxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到(4R,4aR,6R,8S,8aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-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：

  乙酸酐 、 methyl (methyl 3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 、 2,2-二甲氧基丙烷 在 吡啶 、 对甲苯磺酸 作用下， 生成 (4R,4aR,6R,8S,8aR)-8-Acetoxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester 、 5-((4R,5S,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-furan-2-carboxylic acid methyl ester 、 (2R,4S,5R,6R)-4,5-Diacetoxy-6-[(R)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-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