methyl 2-O-benzyl-4,6-O-benzylidene-3-O-methyl-α-D-glucopyranoside | 51433-10-4

• 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: methyl 2-O-benzyl-4,6-O-benzylidene-3-O-methyl-α-D-glucopyranoside
• 英文别名: Methyl 3-O-methyl-2-O-(phenylmethyl)-4,6-O-(phenylmethylene)-I+/--D-glucopyranoside；(4aR,6S,7R,8S,8aR)-6,8-dimethoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 51433-10-4
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: VOTGFKASWGLDPL-PRYCNDIFSA-N

物化性质

• 沸点：
  503.6±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzyl-4,6-O-benzylidene-3-O-methyl-α-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 1,2,4,6-tetra-O-acetate-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
• 作为产物：
  描述：

  methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以64.8%的产率得到methyl 2-O-benzyl-4,6-O-benzylidene-3-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

• ANTICOAGULANT COMPOUNDS
  申请人：Petitou Maurice

  公开号：US20100081708A1

  公开（公告）日：2010-04-01

  The present invention is concerned with anticoagulants (i.e. substances that stop blood from clotting). More specifically, the present invention is concerned with orally available antithrombic oligosaccharides.

  本发明涉及抗凝剂（即阻止血液凝结的物质）。更具体地说，本发明涉及口服可用的抗血栓寡糖。
• [EN] ANTICOAGULANT COMPOUNDS<br/>[FR] COMPOSÉS ANTICOAGULANTS
  申请人：ENDOTIS PHARMA S A

  公开号：WO2008041131A2

  公开（公告）日：2008-04-10

  [EN] The present invention is concerned with anticoagulants (i.e. substances that stop blood from clotting). More specifically, the present invention is concerned with orally available antithrombic oligosaccharides.
  [FR] La présente invention concerne des anticoagulants (à savoir, des substances qui empêchent le sang de coaguler). Plus spécifiquement, la présente invention concerne des oligosaccharides antithrombiques disponibles en prise orale.
• 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.