carboxymethyl-3,4,6-tri-O-acetyl-α-D-galactopyranoside-2-O-lactone | 959925-51-0

• 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: carboxymethyl-3,4,6-tri-O-acetyl-α-D-galactopyranoside-2-O-lactone
• 英文别名: [(4aS,6R,7S,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: 959925-51-0
• 化学式: C₁₄H₁₈O₁₀
• 分子量: 346.291
• InChiKey: JINFPDSYNZKVCX-YTLQFRNZSA-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：

  carboxymethyl-3,4,6-tri-O-acetyl-α-D-galactopyranoside-2-O-lactone 在 copper(I) iodide supported on Amberlyst A-21 resin 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 {[N-(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]carbamoyl}methyl 3,4,6-tri-O-acetyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.11.060
• 作为产物：
  描述：

  2-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid 在 吡啶 、 甲醇 、 水 作用下， 反应 30.0h， 生成 carboxymethyl-3,4,6-tri-O-acetyl-α-D-galactopyranoside-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。