methyl 2,3,6-tri-O-benzyl-4-O-methyl-α-D-galactopyranoside | 55697-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-methyl-α-D-galactopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2,5-dimethoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 55697-55-7
• 化学式: C₂₉H₃₄O₆
• 分子量: 478.585
• InChiKey: RPTRCWBEZRNPJP-LLQHYSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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 2,3,6-tri-O-benzyl-4-O-methyl-α-D-galactopyranoside 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 methyl 4-O-methyl-α-D-galactopyranoside
  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 2,3,6-tri-O-benzyl-α-D-galactopyranoside 、 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99.9%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-methyl-α-D-galactopyranoside
  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

• Novel alpha-glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0389723A1

  公开（公告）日：1990-10-03

  This invention relates to novel N-derivatives, of 1,4-di-­deoxy-1,4-imino-L-arabinitol (I), to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes. wherein n is zero, one or two, and R is a glycosyl or etherified or acylated glycosyl radical containing from 1 to 3 hexose or pentose units, said glycosyl radical optionally bearing an ether or ester derivative of the hydroxyl moiety located on the anomeric carbon atom.

  本发明涉及新颖的1,4-二脱氧-1,4-亚氨基-L-阿拉伯糖醇（I）的N-衍生物，涉及其制备方法及其最终用途，特别是作为治疗糖尿病的用途。 其中n为0、1或2，R为含有1至3个己糖或戊糖单元的糖基或醚化或酰化的糖基基团，所述糖基基团任选地在其异头碳原子上的羟基部分带有醚或酯衍生物。
• Novel SGLT inhibitors
  申请人：Nomura Sumihiro

  公开号：US20080027014A1

  公开（公告）日：2008-01-31

  Novel compounds of formula (A) or a pharmaceutically acceptable salt thereof: wherein symbols are as defined in claims, which are useful as SGLT inhibitors and for treatment of diabetes and related diseases.

  化合物的新颖结构式（A）或其药学上可接受的盐： 其中符号如权利要求中所定义，这些化合物可用作SGLT抑制剂，用于治疗糖尿病及相关疾病。
• Novel Alpha-glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0345104A2

  公开（公告）日：1989-12-06

  This invention relates to novel N-derivatives of 1-deoxy-nojirimycin (1) to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes. wherein n is zero, one or two, and R is a glycosyl or etherified or acylated glycosyl radical containing from 1 to 3 hexose or pentose units, said glycosyl radical optionally bearing an ether or ester derivative of the hydroxyl moeity located on the anomeric carbon atom of the terminal hexose or pentose moeity.

  本发明涉及 1-脱氧-野尻霉素（1）的新型 N 衍生物及其制备工艺和最终应用，特别是在糖尿病治疗中的应用。 其中 n 为 0、1 或 2，R 为含有 1 至 3 个己糖或戊糖单元的糖基或醚化或酰化的糖基，所述糖基任选带有位于末端己糖或戊糖单元的异构碳原子上的羟基的醚或酯衍生物。
• Alpha-glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0422975B1

  公开（公告）日：1994-07-27
• NOVEL $g(a)-GLUCOSIDASE INHIBITORS
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0532668A1

  公开（公告）日：1993-03-24