(N-benzylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside | 1269663-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (N-benzylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: N-benzylcarbamoylmethyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
• CAS: 1269663-97-9
• 化学式: C₂₁H₂₇NO₁₀
• 分子量: 453.446
• InChiKey: CYMZYTZTKIWACN-MLZLACJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.17
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  146.69
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (N-benzylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside 在 乙酸酐 、 二甲基亚砜 作用下， 反应 16.0h， 以96%的产率得到(N-benzylcarbamoyl)methyl 3,6-di-O-acetyl-4-deoxy-α-D-glycero-hex-3-enopyranosid-2-ulose
  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：

  苄胺 、 3,4,6-tri-O-acetyl carboxymethyl-α-D-glucopyranoside-2-O-lactone 以 氘代氯仿 、 环己烷 为溶剂， 反应 72.0h， 以90%的产率得到(N-benzylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  新型C-糖基双环内酯的合成与应用

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2015.07.017