methyl 3,4,6-tri-O-benzoyl-2-O-methyl-α-D-glucopyranoside | 116144-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzoyl-2-O-methyl-α-D-glucopyranoside
• 英文别名: methyl 3,4,6-tri-O-benzoyl-2-O-methyl-α-D-glucopyranose；[(2R,3R,4S,5R,6S)-3,4-dibenzoyloxy-5,6-dimethoxyoxan-2-yl]methyl benzoate
• CAS: 116144-00-4
• 化学式: C₂₉H₂₈O₉
• 分子量: 520.536
• InChiKey: PADWNQOGUFDQIK-YVXTWPRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-benzoyl-2-O-methyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以20 mg的产率得到methyl 2-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  非质子介质中五邻苯甲酰基-α-d-吡喃葡萄糖的氨解作用 分离产物的表征以及11种N-苯甲酰基-d-呋喃呋喃糖胺衍生物的构象分析

  摘要：

  摘要五-O-苯甲酰基-α-d-吡喃葡萄糖与氯仿-1,4-二恶烷-液氨反应生成1,1-双（苯甲酰胺基）-6-O-苯甲酰基-1-脱氧-d-葡萄糖醇（ 29.0％），N-苯甲酰基-α-d-葡萄糖呋喃糖胺的三部分苯甲酰化衍生物（23.6％），N-苯甲酰基-二-O-苯甲酰基-β-d-葡萄糖呋喃糖胺的一小部分（0.2％）和四部分α-d-吡喃葡萄糖的苯甲酰化衍生物（9.9％）。通过化学和光谱学方法建立了迄今未知的产物的结构及其端基构型。N-苯甲酰基-d-葡萄糖呋喃糖胺的两种异构体在溶液中的构象，从氨解反应中分离出的部分苯甲酰化衍生物以及各种化合物的过氧乙酰基衍生物均通过1H-nmr光谱法进行了分析。

  DOI：

  10.1016/0008-6215(87)85006-1
• 作为产物：
  描述：

  Methyl-4,6-O-benzyliden-2-O-methyl-α-D-glucopyranosid 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 methyl 3,4,6-tri-O-benzoyl-2-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084

文献信息

• Ammonolysis of penta-O-benzoyl-α-d-glucopyranose in an aprotic medium. Characterization of the products isolated, and conformational analysis of eleven N-benzoyl-d-glucofuranosylamine derivatives
  作者：Amelia E. Salinas、Jorge F. Sproviero、Venancio Deulofeu

  DOI：10.1016/0008-6215(87)85006-1

  日期：1987.12

  Abstract The reaction of penta-O-benzoyl-α- d -glucopyranose with chloroform-1,4-dioxane-liquid ammonia gave 1,1-bis(benzamido)-6-O-benzoyl-1-deoxy- d -glucitol (29.0%), three partially benzoylated derivatives of N-benzoyl-α- d -glucofuranosylamine (23.6%), a small proportion of N-benzoyl-di-O-benzoyl-β- d -glucofuranosylamine (0.2%), and four partially benzoylated derivatives of α- d -glucopyranose

  摘要五-O-苯甲酰基-α-d-吡喃葡萄糖与氯仿-1,4-二恶烷-液氨反应生成1,1-双（苯甲酰胺基）-6-O-苯甲酰基-1-脱氧-d-葡萄糖醇（ 29.0％），N-苯甲酰基-α-d-葡萄糖呋喃糖胺的三部分苯甲酰化衍生物（23.6％），N-苯甲酰基-二-O-苯甲酰基-β-d-葡萄糖呋喃糖胺的一小部分（0.2％）和四部分α-d-吡喃葡萄糖的苯甲酰化衍生物（9.9％）。通过化学和光谱学方法建立了迄今未知的产物的结构及其端基构型。N-苯甲酰基-d-葡萄糖呋喃糖胺的两种异构体在溶液中的构象，从氨解反应中分离出的部分苯甲酰化衍生物以及各种化合物的过氧乙酰基衍生物均通过1H-nmr光谱法进行了分析。
• Synthesis of Monomethyl Derivatives of<i>P</i>-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases
  作者：Wataru Hakamata、Toshiyuki Nishio、Reiko Sato、Takahiro Mochizuki、Kazuya Tsuchiya、Maki Yasuda、Tadatake Oku

  DOI：10.1080/07328300008544084

  日期：2000.1

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.