methyl 4,6-O-benzylidene-2,3-di-O-(tert-butyloxycarbonylmethyl)-α-D-glucopyranoside

• 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: methyl 4,6-O-benzylidene-2,3-di-O-(tert-butyloxycarbonylmethyl)-α-D-glucopyranoside
• 英文别名: tert-butyl 2-[[(2R,4aR,6S,7R,8S,8aR)-6-methoxy-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]acetate
• 化学式: C₂₆H₃₈O₁₀
• 分子量: 510.582
• InChiKey: APARTTYARLDYAZ-OWJFPWAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2,3-di-O-(tert-butyloxycarbonylmethyl)-α-D-glucopyranoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以80%的产率得到methyl 4,6-O-benzylidene-2,3-di-O-(2-hydroxyethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate-based aza-macrocycles by Richman-Atkins cyclization of glucopyranose precursors

  摘要：

  2, 3-Di-omega-halo-as well as 2, 3-di-omega-toluenesulfonamide-alkylated glucopyranoside derivatives were prepared. Their condensation with alpha,omega-bis-toluenesulfonamide components under varying Richman Atkins conditions with alkali carbonate in DMF led to carbohydrate-linked aza-macrocycles displaying 14-, 17-, 18-, 21-, 24-, and 25-membered ring structures. Isomeric aza-macrocylic coronands of 20-as well as 30-membered ring size containing two saccharides could be obtained employing Richman-Atkins condensations of two functionalized sugar building units. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2016.11.016
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以54%的产率得到methyl 4,6-O-benzylidene-2,3-di-O-(tert-butyloxycarbonylmethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate-based aza-macrocycles by Richman-Atkins cyclization of glucopyranose precursors

  摘要：

  2, 3-Di-omega-halo-as well as 2, 3-di-omega-toluenesulfonamide-alkylated glucopyranoside derivatives were prepared. Their condensation with alpha,omega-bis-toluenesulfonamide components under varying Richman Atkins conditions with alkali carbonate in DMF led to carbohydrate-linked aza-macrocycles displaying 14-, 17-, 18-, 21-, 24-, and 25-membered ring structures. Isomeric aza-macrocylic coronands of 20-as well as 30-membered ring size containing two saccharides could be obtained employing Richman-Atkins condensations of two functionalized sugar building units. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2016.11.016

文献信息

• Mild Selective Hydrolysis of Acetals in Carbohydrates
  作者：Alessandra Gomes Cioletti、Ricardo José Alves、José Dias de Souza Filho、Josiano Gomes Chaves、Maria Auxiliadora Fontes Prado

  DOI：10.1080/00397910008087251

  日期：2000.6

  Abstract A simple and inexpensive methodology for the selective hydrolysis of acetals using hydrogen chloride as catalyst is described.

  摘要 描述了一种使用氯化氢作为催化剂选择性水解缩醛的简单且廉价的方法。