methyl 2,3,6-Tri-O-Benzyl-4-Deoxy-4-Formyl-α-D-Gluco-Pyranoside | 127214-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3,6-Tri-O-Benzyl-4-Deoxy-4-Formyl-α-D-Gluco-Pyranoside
• 英文别名: Methyl 2,3,6,-tri-O-benzyl-4-deoxy-4-formyl-α-D-glucopyranoside；METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-FORMYL-α-D-GLUCOPYRANOSIDE；Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-glucopyranoside；(2S,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane-3-carbaldehyde
• CAS: 127214-51-1
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: SPVINATXNPEEEO-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 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-Deoxy-4-Formyl-α-D-Gluco-Pyranoside 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以87%的产率得到METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE
  参考文献：
  名称：

  立体效应不是立体异构糖苷水解速率差异的原因。

  摘要：

  [结构：见正文]爱德华（Edward）于1955年根据在过渡状态中空间位阻得到缓解的观点，对为什么轴向取代基的糖苷比赤道取代基的糖苷具有更高的反应性做出了长期而合理的解释。我们使用模型化合物5、6、8和10得出结论，表明空间位阻不是糖苷水解的控制因素。

  DOI：

  10.1021/ol030081e
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-cyano-4-deoxy-α-D-glucopyranoside 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 以72%的产率得到methyl 2,3,6-Tri-O-Benzyl-4-Deoxy-4-Formyl-α-D-Gluco-Pyranoside
  参考文献：
  名称：

  Synthesis of an 1′-Azasugar Analogue of Maltose

  摘要：

  甲基1′-氮杂麦芽糖苷（3）是通过16步合成法从左旋葡糖酸内酯和D-半乳糖合成得到的。研究发现，甲基1′-氮杂麦芽糖苷（3）能够抑制葡萄糖淀粉酶，其Ki值为0.63微摩尔。

  DOI：

  10.1055/s-2001-10799

文献信息

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

  公开号：EP0390674A1

  公开（公告）日：1990-10-03

  This invention relates to novel N-derivatives of 1,4-di­deoxy-1,4-imino-L-arabinitol, to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes.

  本发明涉及 1,4-二脱氧-1,4-亚氨基-L-阿拉伯糖醇的新型 N-衍生物、其制备工艺及其最终应用，特别是在治疗糖尿病方面的应用。
• Preuss, Rainer; Jung, Karl-Heinz; Schmidt, Richard R., Liebigs Annalen der Chemie, 1992, # 4, p. 377 - 382
  作者：Preuss, Rainer、Jung, Karl-Heinz、Schmidt, Richard R.

  DOI：——

  日期：——
• Preferred Conformation of <i>C</i>-Lactose at the Free and Peanut Lectin Bound States
  作者：R. Ravishankar、A. Surolia、M. Vijayan、Sungtaek Lim、Yoshito Kishi

  DOI：10.1021/ja982193k

  日期：1998.11.1

  A conformational analysis of methyl alpha-C-lactoside (5) is carried out (Table 1), which suggests the preferred solution conformation of 5 to be described as a mixture of conformers A (phi = 300 degrees; psi = 60 degrees) and B (phi = 300 degrees; psi = 300 degrees) to a first approximation. Applying a modified Karplus equation for the vicinal coupling constants observed for the H.a and H.1' protons of 5, the dihedral angle (phi = 0.5'-C.1'-C.a-C.4) was deduced to be approximately +280 degrees. Nuclear Overhauser effect (NOE) experiments were then conducted on 5-D-2 and its parent methyl alpha-O-lactoside in a 7:3 mixture of pyridine-d(5) and methanol-d(4), qualitatively demonstrating that the conformational characteristics of both methyl alpha-C- and alpha-O-lactosides at the free states are represented as a mixture of two conformers A and B, but their relative population may be different. Through X-ray analysis, it has been definitively established that the conformation (phi = 297(7)degrees and psi = 120(2)degrees) of C-lactose bound to peanut lectin is practically identical to the conformation (phi = 291(6)degrees and psi = 118(9)degrees) of its parent O-lactose bound to the same protein.
• Alpha-glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0422975B1

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

  公开号：EP0532668B1

  公开（公告）日：1995-11-15