methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside | 64605-18-1

• 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 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside
• 英文别名: (4aR,6S,7S,8S,8aR)-6,7-dimethoxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 64605-18-1
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: TZSPBNISVURBAP-GQTGZYIQSA-N

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 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside 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 (2S,3R,4S,5S,6R)-6-(乙酰氧基甲基)-3-甲氧基四氢-2H-吡喃-2,4,5-三乙酸三酯
  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 endo-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  糖醛酸甲基醚的合成。三、甲基（甲基α-D-吡喃甘露糖苷）糖醛酸及其2-和4-0-甲基醚的合成

  摘要：

  甲基（α-D-吡喃甘露糖苷）糖醛酸甲酯及其2-和4-0-甲基醚的合成是通过三氧化铬氧化相应的α-D-吡喃甘露糖苷的O-苄基和O-亚苄基衍生物来实现的，用重氮甲烷酯化，然后通过催化氢解消除保护性苄基或亚苄基。

  DOI：

  10.1007/bf00575690

文献信息

• Synthesis of 2-O-methyl-d-rhamnose, a constituent of a bacterial lipopolysaccharide
  作者：András Lipták

  DOI：10.1016/s0008-6215(00)80550-9

  日期：1982.9
• 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.
• Synthesis of methyl ethers of uronic acids. III. Synthesis of methyl (methyl α-D-mannopyranosid) uronate and its 2- and 4-0-methyl ethers
  作者：V. I. Grishkovets、A. E. Zemlyakov、V. Ya. Chirva

  DOI：10.1007/bf00575690

  日期：1983.7

  The synthesis of methyl (methyl α-D-mannopyranosid)uronate and its 2- and 4-0-methyl ethers has been effected by the chromium trioxide oxidation of the corresponding O-benzyl and O-benzylidene derivatives of methyl α-D-mannopyranoside, esterification with diazomethane, and subsequent elimination of the protective benzyl or benzylidene groups by catalytic hydrogenolysis.

  甲基（α-D-吡喃甘露糖苷）糖醛酸甲酯及其2-和4-0-甲基醚的合成是通过三氧化铬氧化相应的α-D-吡喃甘露糖苷的O-苄基和O-亚苄基衍生物来实现的，用重氮甲烷酯化，然后通过催化氢解消除保护性苄基或亚苄基。