(N-propargylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside | 602302-76-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (N-propargylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: (N-propargylcarbamoyl)methyl-3,4,6-tri-O-acetyl-α-D-glucopyranoside；[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-hydroxy-6-[2-oxo-2-(prop-2-ynylamino)ethoxy]oxan-2-yl]methyl acetate
• CAS: 602302-76-1
• 化学式: C₁₇H₂₃NO₁₀
• 分子量: 401.37
• InChiKey: GCEOCZNUOLZEIY-NHMWIVBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (N-propargylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 48.0h， 以91%的产率得到(N-propargylcarbamoyl)methyl α-D-glucopyranoside
  参考文献：
  名称：

  羧甲基糖苷内酯（CMGLs）：碳水化合物部分的结构变异

  摘要：

  从烯丙基糖苷合成具有异头构型，保护基团（乙酰基或苄基）和呋喃糖基或吡喃糖基环的新的基于葡萄糖和半乳糖的双环内酯，并将其用于制备一系列新的糖基化炔烃酰胺。

  DOI：

  10.1016/j.tetasy.2007.09.007
• 作为产物：
  描述：

  在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 (N-propargylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  羧甲基糖苷内酯（CMGLs）：碳水化合物部分的结构变异

  摘要：

  从烯丙基糖苷合成具有异头构型，保护基团（乙酰基或苄基）和呋喃糖基或吡喃糖基环的新的基于葡萄糖和半乳糖的双环内酯，并将其用于制备一系列新的糖基化炔烃酰胺。

  DOI：

  10.1016/j.tetasy.2007.09.007

文献信息

• Synthesis of new mono- and disaccharidic carboxymethylglycoside lactones (CMGLs) and their use toward 1,2-bisfunctionalized carbohydrate synthons
  作者：Rouba Cheaib、Arkadiusz Listkowski、Stéphane Chambert、Alain Doutheau、Yves Queneau

  DOI：10.1016/j.tetasy.2008.07.016

  日期：2008.8

  A general and convenient access to mono- and disaccharidic carboxymethyl glycoside lactones (CMGLs) is described. By taking advantage of the free OH at the 2-position, obtained after the opening of CMGLs by amines, the synthesis of a series of new 1,2-bisfunctionalized carbohydrate synthons is reported.

  描述了单和二糖基羧甲基糖苷内酯（CMGLs）的一般和方便访问。通过利用由胺打开CMGL之后在2-位获得的游离OH，报道了一系列新的1,2-双官能化碳水化合物合成子的合成。
• Straightforward Route for Anchoring a Glucosyl Moiety onto Nucleophilic Species:  Reaction of Amines and Alcohols with Carboxymethyl 3,4,6-Tri-<i>O</i>-acetyl-α-<scp>d</scp>-glucopyranoside 2-<i>O</i>-Lactone
  作者：Stéphane Trombotto、Mathieu Danel、Juliette Fitremann、Alain Bouchu、Yves Queneau

  DOI：10.1021/jo0300237

  日期：2003.8.1

  The base-catalyzed reaction of carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone (prepared from isomaltulose) with amino acids and fatty amines under basic catalysis gave a series of new pseudoglucopeptides, nonionic amphiphiles, and polymerizable derivatives. The same reaction applied to alcohols provided the corresponding 2-(alpha-D-glucopyranosyloxy)acetyl esters with either basic

  在碱性催化下，羧甲基3,4,6-三-O-乙酰基-α-D-吡喃葡萄糖苷2-O-内酯（由异麦芽酮糖制备）与氨基酸和脂肪胺的碱催化反应产生了一系列新的假葡萄糖肽，非离子两亲物和可聚合衍生物。应用于醇的相同反应提供了带有碱性或酸性催化剂的相应的2-（α-D-吡喃葡萄糖基氧基）乙酰基酯。
• Carboxymethyl glycoside lactone (CMGL) synthons: Scope of the method and preliminary results on step growth polymerization of α-azide-ω-alkyne glycomonomers
  作者：Jie Chen、Yong Miao、Stéphane Chambert、Julien Bernard、Etienne Fleury、Yves Queneau

  DOI：10.1007/s11426-010-4058-0

  日期：2010.9

  Carboxymethyl glycoside lactones (CMGLs) are bicyclic synthons which open readily for accessing new types of pseudo-glycoconjugates, such as sugar-amino acid hybrids, neoglycolipids, pseudodisaccharides, and membrane imaging systems. After lactone opening, free OH-2 is available for further functionalization, leading to 1,2-bisfunctionalized derivatives. This strategy is illustrated herein with new polymerizable systems of the AB type bearing both azide and alkyne functions prepared from α or β gluco-CMGL synthons. After the reaction of lactones with propargylamine, an azido group was introduced by two different sequences leading to either the 2-manno-azido or the 6-gluco-azido products. The capability of these AB monomers to undergo step growth polymerization through copper(I) catalyzed alkyne-azide cycloaddition (CuAAC) and generate glycopolytriazoles was evidenced.

  羧甲基糖苷内酯（CMGLs）是双环合成单体，能迅速打开以获取新型伪糖苷结合物，如糖-氨基酸杂交物、新型糖脂、伪二糖和膜成像系统。经过内酯开环后，自由的OH-2可用于进一步的功能化，生成1,2-双官能化衍生物。本文中通过一种新型的AB型聚合系统进行了说明，该系统具有叠氮和炔烃功能，来源于α或β葡萄糖-CMGL合成单体。在内酯与丙炔胺反应后，通过两种不同的序列引入了叠氮基团，得到了2-甘露糖叠氮或6-葡萄糖叠氮产物。这些AB单体通过铜(I)催化的炔烃-叠氮环加成反应（CuAAC）进行分步增长聚合的能力得到了证实，从而生成了糖聚三嗪。
• Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity
  作者：Nuno M. Xavier、Margarida Goulart、Ana Neves、Jorge Justino、Stéphane Chambert、Amélia P. Rauter、Yves Queneau

  DOI：10.1016/j.bmc.2010.11.060

  日期：2011.1

  The synthesis of a series of pyranoid derivatives comprising a conjugated carbonyl function and related triazole derivatives, structurally suitable for bioactivity evaluation, was achieved in few steps starting from readily available carboxymethyl glycoside lactones (CMGL). 3-Enopyranosid-2-uloses were generated by oxidation/elimination of tri-O-acylated 2-hydroxy pyranosides. Subsequent Wittig olefination provided stereoselectively 2-C-branched-chain conjugated dienepyranosides with (E)-configuration around the exocyclic double bond. A heterogeneous CuI/Amberlyst-catalyzed 'click' chemistry protocol was used to convert glycosides bearing a propargyl moiety into the corresponding 1,2,3-triazoles. These new molecules were screened for their in vitro antibacterial and antifungal activities and those containing conjugated carbonyl systems demonstrated the best efficacy. (N-Dodecylcarbamoyl)methyl enone glycerosides were the most active ones among the enones tested. The alpha-anomer displayed very strong activities against Bacillus cereus and Bacillus subtilis and strong activity toward Enterococcus faecalis and the fungal pathogen Penicillium aurantiogriseum. The corresponding beta-anomer presented a very strong inhibitory effect against two fungal species (Aspergillus niger and P. aurantiogriseum). (N-Dodecyl-/N-propargyl/or N-benzylcarbamoyl) methyl dienepyranosides exhibited selectively a strong activity toward E. faecalis. Further acute toxicity evaluation indicated low toxic effect of the (N-dodecylcarbamoyl)methyl enone glyceroside alpha-anomer and of the carbamoylmethyl dienepyranosides N-protected with propargyl or benzyl groups. (C) 2010 Elsevier Ltd. All rights reserved.