methyl-α,β-D-mannopyranoside | 51023-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-α,β-D-mannopyranoside
• 英文别名: 1-methyl-D-mannopyranoside；methyl D-mannopyranoside；methy D-mannopyranoside；methyl mannoside；methyl D-mannoside；methylmannoside；(2R,3S,4S,5S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 51023-63-3
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: HOVAGTYPODGVJG-BWSJPXOBSA-N

物化性质

• 熔点：
  α type 193-194 β type 74-75
• 溶解度：
  Easily soluble (water), slightly soluble (ethanol)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl-α,β-D-mannopyranoside 在 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 19.17h， 生成 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activity

  摘要：

  Digitoxigenin alpha-L-, beta-L-, alpha-D-, and beta-D-glucosides; alpha-L-, beta-L-, alpha-D-, and beta-D-mannosides; and alpha-L- and beta-L-rhamnosides were stereoselectively synthesized from the corresponding sugar tetrabenzyl trichloroacetimidates. The Na+,K+-ATPase receptor inhibitory activities of these glycosides (as a measure of receptor binding) were compared with those of digitoxigenin, digitoxigenin 6'-hydroxy-beta-D-digitoxoside, digitoxigenin beta-D-galactoside, and digitoxigenin beta-D-digitoxoside. The observed activities reveal that a given sugar substituent may have a role in binding of some glycoside stereoisomers, but not others. With alpha-L- and possibly beta-L-rhamnosides, the 5'-CH3 and 4'-OH appear to have a predominant role in binding to the Na+,K+-ATPase receptor. Addition of a 6'-OH to form the corresponding mannosides dramatically disrupts the effect of both the 5'-CH3 and 4'-OH in prompting receptor binding of the alpha-L isomer. However, with the beta-L isomer, some influence of 4'-OH, 3'-OH, and 2'-OH binding remains. With beta-D-glycosides, binding via the "5'-CH3 site" appears to be of little importance and addition of a 6'-OH diminishes activity only slightly. With these beta-D-glycosides, an equatorial 4'-OH, axial 3'-OH, and equatorial 2'-OH groups appear to contribute to binding.

  DOI：

  10.1021/jm00160a025
• 作为产物：
  描述：

  1-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)chlorogentisyl alcohol 在 盐酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 methyl-α,β-D-mannopyranoside
  参考文献：
  名称：

  Microbial Mannosidation of Bioactive Chlorogentisyl Alcohol by the Marine-Derived Fungus Chrysosporium synchronum

  摘要：

  从海洋来源的真菌曲霉（Aspergillus sp.）中分离得到的生物活性化合物氯羟苯丙醇（1）的生物转化研究已被进行。通过海洋来源的真菌金孢虫草（Chrysosporium synchronum）对氯羟苯丙醇进行制备规模的发酵，成功分离出了一种新的糖苷代谢产物，即1-O-（α-D-甘露糖苷）氯羟苯丙醇（2）。通过对详尽的光谱数据分析、化学反应和化学合成，确定了新代谢产物的立体结构。化合物1和2对1,1-二苯基-2-苦基肼基自由基（DPPH）显示出显著的自由基清除活性，其IC50值分别为1.0和4.7 μM。化合物1和2的活性均优于阳性对照L-抗坏血酸（IC50为20.0 μM）。

  DOI：

  10.1248/cpb.59.499

文献信息

• A New Method for the Stereoselective Synthesis of α- and β-Glycosylamines Using the Burgess Reagent
  作者：K. C. Nicolaou、Scott A. Snyder、Annie Z. Nalbandian、Deborah A. Longbottom

  DOI：10.1021/ja049293c

  日期：2004.5.1

  Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts. In this communication, we report an operationally simple method for the synthesis of both α- and β-glycosylamines using the Burgess reagent that overcomes

  尽管从生物学和医学的角度来看，糖基胺构成了一组重要的碳水化合物，但它们的合成方法通常缺乏底物的通用性和/或导致可变的立体选择性，尤其是在复杂的环境中。在这篇通讯中，我们报告了一种使用 Burgess 试剂合成 α- 和 β- 糖基胺的操作简单的方法，该方法以最少的合成步骤克服了许多这些限制。
• New Uses for the Burgess Reagent in Chemical Synthesis: Methods for the Facile and Stereoselective Formation of Sulfamidates, Glycosylamines, and Sulfamides
  作者：K. C. Nicolaou、Scott A. Snyder、Deborah A. Longbottom、Annie Z. Nalbandian、Xianhai Huang

  DOI：10.1002/chem.200400503

  日期：2004.11.19

  Although the Burgess reagent (methoxycarbonylsulfamoyltriethylammonium hydroxide, inner salt) has found significant use in chemical synthesis as a dehydrating agent, almost no work has been directed towards its potential in other synthetic applications. As this article will detail, we have found that the Burgess reagent is remarkably effective at accomplishing a number of non-dehydrative synthetic

  尽管Burgess试剂（甲氧基羰基氨磺酰基三乙铵氢氧化物，内盐）已发现在化学合成中作为脱水剂具有重要用途，但几乎没有工作针对其在其他合成应用中的潜力。正如本文将要详细介绍的那样，我们发现，将Burgess试剂应用于适当的底物上，例如从1,2-二醇或环氧醇，α-和C-形成氨基磺酸盐时，在完成许多非脱水合成任务方面非常有效。来自碳水化合物的β-糖胺和来自1,2-氨基醇的环状磺酰胺 除了描述这些新反应歧管的功能之外，我们还描述了一组替代的Burgess型试剂的构造，这些试剂进一步扩展了这些新反应的范围。
• Montmorillonite K-10 as a Reusable Catalyst for Fischer Type of Glycosylation under Microwave Irradiation
  作者：Dipak K. Roy、Manobjyoti Bordoloi

  DOI：10.1080/07328300802107437

  日期：2008.7

  Montmorillonite K10 catalyzed Fischer type glycosylation was studied for various monosacharides with different alcohols under microwave irradiation. The method was found to be efficient, economic, simple and time saving and the catalyst montmorillonite K-10 was reused three times without loss of catalytic activity and anomeric selectivity. With glycerol, the method gave products glycosylated at primary

  在微波辐射下，研究了蒙脱石K10催化的费歇尔型糖基化反应，研究了用不同醇制得的各种单糖。发现该方法是有效，经济，简单和省时的，并且催化剂蒙脱石K-10可重复使用三次，而不会损失催化活性和端基异构体选择性。对于甘油，该方法仅产生在伯醇处糖基化的产物。
• TARGETED NANOPREPARATION OF MANNOSE, AND PREPARATION THEREFOR AND APPLICATION THEREOF
  申请人：CHENGDU RIBOCURE PHARMATECH COMPANY LIMITED

  公开号：US20210196832A1

  公开（公告）日：2021-07-01

  The present invention relates to the field of pharmaceutical preparations, in particular, to a mannose modified targeting nano-preparations, a composition for preparing nano-preparations, a targeting element, a targeting vector, a prepared targeting drug and a preparation method and the application thereof. The described nano-preparations with targeting function is composed of the targeting ligand mannose and its derivatives, nano-preparations and main drug components, and the described targeting material is linked with the spacer material, and then linked with the nano-preparations material to prepare the nano-preparations. The targeting nano-preparations in the present invention has good targetability of mannose receptor, can effectively bond with mannose receptor on target cell. Moreover, the preparation method has universality, can be used for synthesizing a variety of targeting nano-preparations, and is conducive to purification and characterization.

  本发明涉及制药制剂领域，具体地说，涉及一种甘露糖修饰靶向纳米制剂，用于制备纳米制剂的组合物，靶向元素，靶向载体，制备的靶向药物以及其制备方法和应用。所述具有靶向功能的纳米制剂由靶向配体甘露糖及其衍生物、纳米制剂和主要药物成分组成，所述靶向材料与间隔材料连接，然后与纳米制剂材料连接以制备纳米制剂。本发明的靶向纳米制剂具有良好的甘露糖受体靶向性，能够有效地与靶细胞上的甘露糖受体结合。此外，制备方法具有普适性，可用于合成各种靶向纳米制剂，并有利于纯化和表征。
• [EN] IMMUNOTHERAPIES FOR MALIGNANT, NEURODEGENERATIVE AND DEMYELINATING DISEASES BY THE USE OF TARGETED NANOCARRIERS<br/>[FR] IMMUNOTHÉRAPIES UTILISANT DES NANOVECTEURS CIBLÉS POUR TRAITER DES MALADIES MALIGNES, NEURODÉGÉNÉRATIVES ET DÉMYÉLINISANTES
  申请人：RODOS BIOTARGET GMBH

  公开号：WO2017017148A1

  公开（公告）日：2017-02-02

  The present invention relates to the targeted delivery of the active generic antiproliferative and anti-inflammatory agents gemcitabine, paclitaxel and/or curcumin preferentially or exclusively to antigen-presenting cells (APCs) of the immune system by means of encapsulation into a lipid-based nanocarrier, the CLR-TargoSphere, which is surface-labeled with a Fucose-derivative ligand that exclusively targets C-type lectin receptors (CLRs) on APCs to deliver the active agents intracellularly to myeloid dendritic cells (mDCs), circulating monocytes, macrophages, and tumor-associated macrophages (TAMs) as well as cytotoxic T lymphocytes (CTLs).

  本发明涉及将活性通用抗增殖和抗炎剂吉西他滨、紫杉醇和/或姜黄素通过封装入基于脂质的纳米载体CLR-TargoSphere，实现对免疫系统的抗原呈递细胞（APCs）的靶向递送，该纳米载体的表面标记有靶向APCs上C型凝集素受体（CLRs）的岩藻糖衍生物配体，以将活性剂递送至髓样树突状细胞（mDCs）、循环单核细胞、巨噬细胞以及肿瘤相关巨噬细胞（TAMs）以及细胞毒性T淋巴细胞（CTLs）的细胞内。