methyl 4,6-di-O-methoxybenzylidene-2,3-di-O-methoxybenzyl-α-D-glucopyranoside | 342789-77-9

• 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 4,6-di-O-methoxybenzylidene-2,3-di-O-methoxybenzyl-α-D-glucopyranoside
• 英文别名: methyl 4,6-O-(4-methoxybenzylidene)-2,3-O-di-(4-methoxyphenylmethyl)-α-D-glucopyranoside；(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-(4-methoxyphenyl)-7,8-bis[(4-methoxyphenyl)methoxy]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 342789-77-9
• 化学式: C₃₁H₃₆O₉
• 分子量: 552.621
• InChiKey: XEIZGYYKSHKWSG-YZTFKCKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 4,6-di-O-methoxybenzylidene-2,3-di-O-methoxybenzyl-α-D-glucopyranoside 在 水 、 溶剂黄146 作用下， 反应 0.17h， 生成 methyl 2,3-di-O-(4-methoxyphenylmethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a trigalacturonic acid analogue mimicking the expected transition state in the glycosidases

  摘要：

  A trigalacturonic acid analogue carrying a cyclohexene framework in place of the central pyranose ring was synthesized as a molecular probe for the mechanistic investigation of endo-polygalacturonase 1 (endo-PG 1). Preliminary enzymatic studies revealed that this analogue inhibited endo-PG 1 activity by about 30% at 0.3 mM concentration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.024
• 作为产物：
  描述：

  4-甲氧基溴苄 、 methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以81%的产率得到methyl 4,6-di-O-methoxybenzylidene-2,3-di-O-methoxybenzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a trigalacturonic acid analogue mimicking the expected transition state in the glycosidases

  摘要：

  A trigalacturonic acid analogue carrying a cyclohexene framework in place of the central pyranose ring was synthesized as a molecular probe for the mechanistic investigation of endo-polygalacturonase 1 (endo-PG 1). Preliminary enzymatic studies revealed that this analogue inhibited endo-PG 1 activity by about 30% at 0.3 mM concentration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.024

文献信息

• Novel Synthesis of Enantiomerically Pure Natural Inositols and Their Diastereoisomers
  作者：Hideyo Takahashi、Hisae Kittaka、Shiro Ikegami

  DOI：10.1021/jo001575h

  日期：2001.4.1

  phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion

  已经发现各种肌醇多磷酸盐引发许多重要的生物学过程。尽管在过去的十年中已经发现了这种磷酸肌醇信号系统的知识，但许多因素仍不清楚。由于这个原因，对D-肌醇特别是新颖类似物的供应的需求增加，以更详细地研究这些生物学机制。在此，我们报告了从6-O-乙酰基-5-烯吡喃糖苷开始的肌醇所有非对映异构体的高效合成。发现用催化量的二氯化钯可以有效地进行6-O-乙酰基-5-烯吡喃糖苷到相应的取代的环己酮的转化（费里尔-II重排）。所获得的β-羟基酮的立体选择性还原提供了所有肌醇非对映异构体的前体，具有良好至优异的产率以及高的立体选择性。这些对映体纯的肌醇非对映异构体的良好可及性导致D-肌醇1,4,5-三磷酸和D-肌醇1,3,4,5-四磷酸的有效合成。
• Synthesis of a trigalacturonic acid analogue mimicking the expected transition state in the glycosidases
  作者：Kazunori Yamamoto、Shogo Noguchi、Noboru Takada、Kazuo Miyairi、Masaru Hashimoto

  DOI：10.1016/j.carres.2009.12.024

  日期：2010.3

  A trigalacturonic acid analogue carrying a cyclohexene framework in place of the central pyranose ring was synthesized as a molecular probe for the mechanistic investigation of endo-polygalacturonase 1 (endo-PG 1). Preliminary enzymatic studies revealed that this analogue inhibited endo-PG 1 activity by about 30% at 0.3 mM concentration. (C) 2009 Elsevier Ltd. All rights reserved.