[(2R,4aR,6S,7R,8S,8aR)-7-benzoyloxy-6-methoxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate | 1112986-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: [(2R,4aR,6S,7R,8S,8aR)-7-benzoyloxy-6-methoxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 1112986-37-4
• 化学式: C₂₉H₂₈O₉
• 分子量: 520.536
• InChiKey: ZQSLDTFWMCNNCZ-VLZGMPIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,4aR,6S,7R,8S,8aR)-7-benzoyloxy-6-methoxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate 在 三乙基硅烷 、 palladium 10% on activated carbon 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以90%的产率得到methyl 2,3-di-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  使用三乙基硅烷和 Pd/C 去除碳水化合物衍生物中的亚苄基缩醛和苄醚。

  摘要：

  在室温下，通过在 CH(3)OH 中使用三乙基硅烷和 10% Pd/C 的组合，在催化转移氢化条件下实现了含有亚苄基缩醛和苄基醚的碳水化合物衍生物的清洁脱保护。由它们的亚苄基衍生物以优异的产率制备了多种碳水化合物二醇衍生物。

  DOI：

  10.3762/bjoc.9.9
• 作为产物：
  描述：

  苯甲酸酐 、 methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 copper(II) trifluoroacetate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以61%的产率得到
  参考文献：
  名称：

  Regioselective Benzoylation of 4,6-O-Benzylidene Acetals of Glycopyranosides in the Presence of Transition Metals

  摘要：

  Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides by benzoic anhydride in acetonitrile in the presence of Cu(CF3COO)(2) as a promoter gave 2-benzoates for alpha-D-glucopyranosides and alpha-D-mannopyranosides and 3-benzoates for beta-D-galactopyranosides in good yields with high regioselectivity. Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides of D-galactose and D-mannose by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst in all studied cases led to regioselective 3-O-substitution.

  DOI：

  10.1080/07328303.2014.996291

文献信息

• Regioselective Benzoylation of 4,6-<i>O</i>-Benzylidene Acetals of Glycopyranosides in the Presence of Transition Metals
  作者：Evgeny V. Evtushenko

  DOI：10.1080/07328303.2014.996291

  日期：2015.1.2

  Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides by benzoic anhydride in acetonitrile in the presence of Cu(CF3COO)(2) as a promoter gave 2-benzoates for alpha-D-glucopyranosides and alpha-D-mannopyranosides and 3-benzoates for beta-D-galactopyranosides in good yields with high regioselectivity. Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides of D-galactose and D-mannose by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst in all studied cases led to regioselective 3-O-substitution.
• Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C
  作者：Abhishek Santra、Tamashree Ghosh、Anup Kumar Misra

  DOI：10.3762/bjoc.9.9

  日期：——

  Clean deprotection of carbohydrate derivatives containing benzylidene acetals and benzyl ethers was achieved under catalytic transfer hydrogenation conditions by using a combination of triethylsilane and 10% Pd/C in CH(3)OH at room temperature. A variety of carbohydrate diol derivatives were prepared from their benzylidene derivatives in excellent yield.

  在室温下，通过在 CH(3)OH 中使用三乙基硅烷和 10% Pd/C 的组合，在催化转移氢化条件下实现了含有亚苄基缩醛和苄基醚的碳水化合物衍生物的清洁脱保护。由它们的亚苄基衍生物以优异的产率制备了多种碳水化合物二醇衍生物。