2,3,5-tri-O-acetyl-1-O-(1-naphthyl)-β-D-ribofuranoside | 64691-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-acetyl-1-O-(1-naphthyl)-β-D-ribofuranoside
• CAS: 64691-26-5
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: IXTRJVDIVYCJRR-XRXFAXGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-acetyl-1-O-(1-naphthyl)-β-D-ribofuranoside 在 甲醇 、 氨 作用下， 以91%的产率得到α-naphthyl β-D-ribofuranoside
  参考文献：
  名称：

  O-芳基α，β-d-呋喃核糖苷的合成，高效异构体的生物催化分离及其对Src激酶抑制活性的评估

  摘要：

  已经合成了一系列过乙酰化的O-芳基α，β- d-核呋喃糖苷，并且已经开发了用于分离其端基异构体的有效的生物催化方法，否则通过柱色谱法或其他技术几乎是不可能的。将2,3,5-三-O-乙酰基-1- O-芳基-α，β- d-核呋喃糖苷与固定在硅胶上的Lipozyme®TL IM一起孵育仅导致一个乙酰氧基的选择性脱乙酰，即C -5′- Oα-端基异构体的-乙酰氧基高于分子中存在的两个仲羟基衍生的其他乙酰氧基，也超过三个乙酰基基团（源自β-端基异构体的一个伯羟基和两个仲羟基）。该方法导致容易合成O-芳基d-核呋喃呋喃糖苷的α-和β-端基异构体。筛选所有的芳基呋喃核糖苷抑制Src激酶。1 - O-（3-甲氧基苯基）-β- d-核呋喃糖苷显示出最高的抑制Src激酶的活性（IC 50  = 95.0μM ）。

  DOI：

  10.1016/j.bmc.2012.09.057
• 作为产物：
  描述：

  2,3,5-tri-O-acetyl-1-O-(1-naphthyl)-D-ribofuranoside 在 Lipozyme TL IM-Thermomyces lanuginosus lipase immobilised on silica 作用下， 以 异丙醚 、 正丁醇 为溶剂， 反应 12.5h， 以95%的产率得到
  参考文献：
  名称：

  Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers

  摘要：

  It has been demonstrated that Lipozyme (R) TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5' hydroxyl group of alpha-anomers over the other acyl functions of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranoside. The analysis of results of biocatalytic deacylation reaction revealed that the reaction time decreases with the increase in the acyl chain length from C-1 to C-4. The unique selectivity of Lipozyme (R) TL IM has been harnessed for the separation of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranosides, The lipase mediated selective deacylation methodology has been used for the synthesis of O-aryl alpha-D-ribofuranosides and O-aryl beta-D-ribofuranosides in pure forms, which can be used as chromogenic substrate for the detection of pathogenic microbial parasites containing glycosidases. (C) 2014 Published by Elsevier Inc.

  DOI：

  10.1016/j.bioorg.2014.02.004

文献信息

• FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs
  作者：Hamid Marzag、Guillaume Robert、Maeva Dufies、Khalid Bougrin、Patrick Auberger、Rachid Benhida

  DOI：10.1016/j.ultsonch.2014.05.022

  日期：2015.1

  Phenol derived O-glycosides were synthesized using a direct and convenient O-glycosidation, starting from acetylated sugars in the presence of FeCl3, an inexpensive, mild and benign Lewis acid catalyst. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions leading to the corresponding beta-O-glycosides as the major anomer. Post-synthetic transformations of iodophenol intermediates led to new resveratrol O-glycoside analogs in good overall yields. (C) 2014 Elsevier B.V. All rights reserved.