acetyl 2,4-di-O-acetyl-3-O-allyl-6-deoxy-D-glucopyranoside | 674782-56-0

• 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: acetyl 2,4-di-O-acetyl-3-O-allyl-6-deoxy-D-glucopyranoside
• 英文别名: 1,2,4-tri-O-acetyl-3-O-allyl-6-deoxy-D-glucopyranose；[(2R,3R,4S,5R)-5,6-diacetyloxy-2-methyl-4-prop-2-enoxyoxan-3-yl] acetate
• CAS: 674782-56-0
• 化学式: C₁₅H₂₂O₈
• 分子量: 330.335
• InChiKey: QFJDJPJDFZLGQN-UMZCEYCISA-N

物化性质

• 沸点：
  392.9±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  acetyl 2,4-di-O-acetyl-3-O-allyl-6-deoxy-D-glucopyranoside 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,4-di-O-acetyl-3-O-allyl-6-deoxy-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r
• 作为产物：
  描述：

  乙酸酐 、 3-O-allyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 溶剂黄146 、 三氟乙酸 、 硫酸 作用下， 以 水 为溶剂， 反应 1.0h， 以96%的产率得到acetyl 2,4-di-O-acetyl-3-O-allyl-6-deoxy-D-glucopyranoside
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r

文献信息

• Synthesis of the Pentasaccharide Moiety of Thornasterside A
  作者：Junlong Xiong、Zhichao Lu、Ning Ding、Sumei Ren、Yingxia Li

  DOI：10.1002/ejoc.201300575

  日期：2013.9

  The synthesis of the pentasaccharide moiety of thornasteroside A, the first asterosaponin isolated from starfish in 1978 has been achieved for the first time. Initially, a [3+2] convergent strategy was attempted, but the β(14) glycosidic linkage between galactopyranose (sugar IV) and xylopyranose (sugar II) was formed with a low stereoselectivity and in low yield. Subsequently, a [3+1+1] strategy was

  1978年从海星中分离出的第一个星皂苷，首次实现了刺甾酮A的五糖部分的合成。最初，尝试了 [3+2] 收敛策略，但在吡喃半乳糖（糖 IV）和吡喃木糖（糖 II）之间形成的 β(14) 糖苷键具有低立体选择性和低产率。随后，采用了 [3+1+1] 策略。吡喃半乳糖供体 (18) 在 2 位配备有相邻的参与 Lev (乙酰丙酰基) 基团，首先与三糖受体偶联以构建 β(14) 糖苷键。然后选择性地去除 Lev 基团，随后用过苯甲酰化的 D-吡喃岩藻糖施密特供体进行糖基化，有效地得到所需的五糖。