3-chloropropyl β-d-glucopyranoside | 911652-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloropropyl β-d-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-(3-chloropropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 911652-82-9
• 化学式: C₉H₁₇ClO₆
• 分子量: 256.683
• InChiKey: YQOCWVRMYFLOGE-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 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：

  3-chloropropyl β-d-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 三氟化硼乙醚 、 氢气 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 135.0 ℃ 、405.33 kPa 条件下， 反应 67.0h， 生成 3-chloropropyl-3,4-O-[(2R,3R)-2,3-dimethoxybutane-2,3-diyl]-6-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Polyvalent effect enhances diglycosidic antiplasmodial activity

  摘要：

  An efficient and facile total synthesis of diglycoside Matayoside D isolated from the root bark of Matayba guiattensis with antiplasmodial activity have been accomplished in 11 steps with 5% overall yields starting from commercially available glucose and rhamnose. Furthermore, a class of the diglycosidic derivatives with different lengths of the linker and valences were also prepared and evaluated for their antiplasmodial activities against chloroquine-susceptible (3D7) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Low valent and short linker attached diglycoside show no enhancement of the antiplasmodial activity while polyvalent conjugates showed enhanced antiplasmodial activity with IC50 value at least 20 fold better than that of the corresponding diglycosidic monomer. The polyvalent diglycoside were non-cytotoxic against normal mammalian cells under 50,000 g/L. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.05.069
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 甲醇 、 calcium sulfate 、 氯仿 、 sodium methylate 、 silver(l) oxide 作用下， 生成 3-chloropropyl β-d-glucopyranoside
  参考文献：
  名称：

  Helferich; Schnorr, Justus Liebigs Annalen der Chemie, 1941, vol. 547, p. 201,205

  摘要：

  DOI：

文献信息

• Hydrogen-bond-rich ionic liquids as effective organocatalysts for Diels–Alder reactions
  作者：Karol Erfurt、Ilona Wandzik、Krzysztof Walczak、Karolina Matuszek、Anna Chrobok

  DOI：10.1039/c4gc00380b

  日期：——

  characterisation of new hydrogen-bond-rich ionic liquids and studies of their catalytic performance in Diels–Alder reactions are described. D-Glucose and chloroalcohols were used as the raw materials and as the sources of hydroxyl groups for the synthesis of ionic-liquid cations, whereas weakly coordinating bis(trifluoromethylsulfonyl)imide was used as the anion. The new ionic liquids were analysed by 1H and 13C

  描述了新型富氢键离子液体的合成，表征以及它们在Diels–Alder反应中的催化性能的研究。D-葡萄糖和氯醇被用作合成离子-液体阳离子的原料和羟基的来源，而弱配位的双（三氟甲基磺酰基）酰亚胺被用作阴离子。用1 H和13分析新的离子液体通过13 C NMR光谱和ESI-MS实验，证实了它们的结构。此外，通过差示扫描量热法和热重分析法测得的离子液体的热数据表明，这些化合物在-29°C至-16°C的温度范围内倾向于形成玻璃，并且在环境温度下具有热稳定性。到至少430°C，最有可能是因为存在双（三氟甲基磺酰基）酰亚胺阴离子。研究了离子液体在环戊二烯与马来酸二乙酯或丙烯酸甲酯的模型反应中的性能。所研究的离子液体即使以催化量存在（相对于亲双烯体为4摩尔％）也显示出高活性。离子液体结构中存在的羟基数目的增加导致更高的反应速率。
• Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis
  作者：Jacques Augé、Gwenaëlle Sizun

  DOI：10.1039/b904692e

  日期：——

  Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

  在钪三氟甲磺酸盐催化下，对各种醇与未保护和非活化的单糖进行了直接的糖苷化反应。当使用1-丁基-3-甲基咪唑三氟甲磺酸盐作为绿色溶剂时，糖苷化的反应速率和产率得到了显著提高。该离子液体可至少回收使用三次而不会失去活性。在离子液体中进行反应时，可以显著减少催化剂的用量（低至1 mol%）和糖苷的用量（低至1当量），这为O-糖苷化的直接耦合提供了新的前景，能够在糖苷和游离糖之间实现直接连接。
• Sugar conjugates of pyridinium aldoximes as antidotes against organophosphate poisoning
  作者：Eli Heldman、Yacov Ashani、Lily Raveh、Eliezer S. Rachaman

  DOI：10.1016/s0008-6215(00)90353-7

  日期：1986.8

  ring has been prepared as potential antidotes against organophosphate poisoning. The sugar residue was attached either directly through C-1 or C-6 of the pyranose ring or through a C3 bridge between the glycosyl group and the nitrogen atom of the pyridine moiety. Attachment of a sugar group to the oxime derivative seems to increase the bioavailability of the antidote. The clearance rate of the sugar conjugates

  已经制备了一系列具有与吡啶环缀合的糖的吡啶鎓醛肟，作为对抗有机磷酸盐中毒的潜在解毒剂。糖残基直接通过吡喃糖环的C-1或C-6或通过糖基和吡啶部分的氮原子之间的C3桥连接。糖基与肟衍生物的连接似乎增加了解毒剂的生物利用度。糖缀合物的清除率显着低于其非糖类似物的清除率，因此它们在血液循环中的保留时间更长。与最常用的单肟之一——N-甲基-2-吡啶鎓醛肟肟甲磺酸盐相比，糖衍生物在降低对氧磷诱导的体温过低（在中枢神经系统内受调节）方面更有效。糖类似物的毒性也比非糖类似物低。有些还显示出更高的功效。讨论了糖肟的改善特征的潜在机理以及与糖对肟功能的附着有关的结构要求。
• Straightforward glycosylation of alcohols and amino acids mediated by ionic liquid
  作者：Olivier Monasson、Gwenaëlle Sizun-Thomé、Nadège Lubin-Germain、Jacques Uziel、Jacques Augé

  DOI：10.1016/j.carres.2012.03.004

  日期：2012.5

  Green glycosylation of functionalized alcohols and alpha-amino acids, using an ionic liquid as a recyclable solvent, was performed in one step directly from the unprotected monosaccharide under scandium triflate or ferric chloride catalysis. Pure alpha- and beta-glycosides could be obtained after specific enzymatic hydrolysis. (c) 2012 Elsevier Ltd. All rights reserved.
• US4609478A
  申请人：——

  公开号：US4609478A

  公开（公告）日：1986-09-02