3,4,6-tri-O-acetyl carboxymethyl-α-D-glucopyranoside-2-O-lactone | 314238-23-8

• 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: 3,4,6-tri-O-acetyl carboxymethyl-α-D-glucopyranoside-2-O-lactone
• 英文别名: carboxymethyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside 2-O-lactone；carboxymethyl-3,4,6-tri-O-acetyl-α-D-glucopyranoside-2-O-lactone；gluco-α-CMGL；[(4aS,6R,7R,8S,8aR)-7,8-diacetyloxy-2-oxo-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]dioxin-6-yl]methyl acetate
• CAS: 314238-23-8
• 化学式: C₁₄H₁₈O₁₀
• 分子量: 346.291
• InChiKey: JINFPDSYNZKVCX-LPUQOGTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl carboxymethyl-α-D-glucopyranoside-2-O-lactone 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (N-tetradecylcarbamoyl)methyl α-D-glucopyranoside
  参考文献：
  名称：

  将葡糖基部分锚定在亲核物质上的简单方法：胺和醇与羧甲基3,4,6-三-O-乙酰基-α-D-吡喃葡萄糖苷2-O-内酯的反应。

  摘要：

  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。

  DOI：

  10.1021/jo0300237
• 作为产物：
  描述：

  carboxymethyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 吡啶 、 甲醇 、 水 作用下， 反应 30.0h， 生成 3,4,6-tri-O-acetyl carboxymethyl-α-D-glucopyranoside-2-O-lactone
  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。
• Synthesis and use of new C-glycosyl bicyclic lactones
  作者：Arkadiusz Listkowski、Otman Otman、Stéphane Chambert、Yves Queneau

  DOI：10.1016/j.tetlet.2015.07.017

  日期：2015.8

  New C-glycosyl bicyclic lactones have been synthesized in three steps from glycosyl bromides and used as synthons towards C-glycosyl derivatives which can readily be elaborated to 1,2-bisfunctionalized carbohydrate systems. The method was illustrated with several examples of pseudo conjugates prepared from the new C-glycosyl 1,2-fused pyrano-δ-lactonic building blocks, either with groups such as allyl

  从糖基溴化物以三个步骤合成了新的C-糖基双环内酯，并将其用作对C-糖基衍生物的合成子，所述C-糖基衍生物可以容易地制成1，2-双官能化的碳水化合物体系。用新的C-糖基1,2-稠合的吡喃基-δ-内酯结构基团制备的假缀合物的几个例子说明了该方法，这些基团具有诸如烯丙基或炔丙基这样的基团，具有较大的后续反应性，或者具有更精细的部分，从而导致模型糖氨基酸或假核苷酸糖。
• Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation
  作者：R. Xu、F. Ali-Rachedi、N. M. Xavier、S. Chambert、F. Ferkous、Y. Queneau、S. J. Cowling、E. J. Davis、J. W. Goodby

  DOI：10.1039/c4ob02191f

  日期：——

  The synthesis of glycosteroidal bolaphile biomimics are described along with the liquid-crystalline behaviours as a function of increasing aliphatic composition.

  描述了糖甾类博拉菲生物模拟物的合成，以及液晶行为随着脂肪族成分增加而变化的情况。
• Neutral push-pull chromophores for nonlinear optical imaging of cell membranes
  作者：Cyril Barsu、Rouba Cheaib、Stéphane Chambert、Yves Queneau、Olivier Maury、Davy Cottet、Hartmut Wege、Julien Douady、Yann Bretonnière、Chantal Andraud

  DOI：10.1039/b915654b

  日期：——

  A new class of push-pull molecules was recently identified, based on pyridine dicarboxamide as an electron acceptor group and bearing a fluorenethynyl π-conjugated bridge. The molecules present good second and third order nonlinear properties, with a static quadratic hyperpolarisability μβ (at 1.907 μm) of 320 × 10−48 esu (μβ0 = 249 × 10−48 esu) and a maximum two-photon absorption cross-section of 1146 GM. Starting from this generic structure, we designed a series of eight amphiphilic nonlinear probes, varying the length of the lipophilic tail and the nature of the polar head, and tested their cell membrane affinity by nonlinear optical imaging. A good membrane affinity was observed with probes bearing short alkyl chains and carbohydrate moieties as the polar head, emphasizing the importance of the lipophilic–hydrophilic balance, as well as the role of the polar head. This original approach based on carbohydrate head groups is an important advancement in the design of membrane probes, since these highly versatile functional groups confer adequate hydrophilicity and yet conserve overall molecular neutrality.

  最近，研究人员识别出一种新型的推-拉分子，这些分子以吡啶二羧酰胺作为电子受体基团，具有基于芴炔的π-共轭桥。该分子表现出良好的二次和三次非线性特性，在1.907微米处的静态二次超极化率μβ为320 × 10−48 esu（μβ0 = 249 × 10−48 esu），最大双光子吸收截面为1146 GM。从这个通用结构出发，我们设计了一系列八种两性非线性探针，改变了脂溶性尾部的长度和极性头部的性质，并通过非线性光学成像测试了它们的细胞膜亲和性。我们观察到，具有短链烷基和糖类基团作为极性头的探针表现出良好的膜亲和性，强调了脂溶性与亲水性平衡的重要性，以及极性头部的作用。这种基于糖类头基的原始方法是膜探针设计的重要进展，因为这些高度多功能的基团赋予了适当的亲水性，同时保持整体分子的中性。
• 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。