6-O-(2,3-Epoxypropyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-O-(2,3-Epoxypropyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: 6-O-[(2R,S)-2,3-epoxypropyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose；(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-8-(oxiran-2-ylmethoxymethyl)-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• 化学式: C₁₅H₂₄O₇
• 分子量: 316.351
• InChiKey: PBHXLRBXWLXZLV-PTZRQYDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-O-(2,3-Epoxypropyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium azide 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  受点击化学启发而产生的首批Noscapine糖缀合物†

  摘要：

  已经通过两个连续的步骤，从鸦片植物中发现的一种生物碱-诺斯卡汀开始合成了许多新颖的7- O-诺斯卡汀糖缀合物。第一步是Noscapine的选择性7- O-去甲基化，第二步是随后的炔丙基化，以良好的收率得到7- O-炔丙基基Noscapine（3）。通过包括单晶X射线数据在内的大量光谱数据证实了该结构。研究了发达的Noscapine衍生物3与糖基叠氮化物6a–m的1,3-偶极环加成反应，得到了三唑连接的第二代Noscapine类似物，其糖缀合物形式（8a–m ）以增强Noscapine的治疗功效。

  DOI：

  10.1039/c5ra07321a
• 作为产物：
  描述：

  口服葡萄糖 在 硫酸 、 四丁基溴化铵 、 sodium hydroxide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.67h， 生成 6-O-(2,3-Epoxypropyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis and evaluation of antibacterial and antitumor activities of new galactopyranosylated amino alcohols

  摘要：

  Three series of D-galactose derivatives linked to a lipophilic aminoalcohol moiety were synthesized and their antibacterial activity was evaluated against Mycobacterium tuberculosis and representative species of Gram positive and Gram negative bacteria. Five out of the thirteen tested compounds displayed activity against M. tuberculosis, with a minimal inhibitory concentration (MIC) of 12.5 mu g/mL and seven compounds were active against the four bacterial strains tested. The best results were obtained for amino alcohols 10 and 11 against Staphylococcus epidermidis (MIC = 2 mu g/mL). The antitumor activity was evaluated against three tumor cell lines (MCF-7, HeLa and MO59J) and compared to the normal cell line GM07492A. The results showed that the lowest IC50 values were observed for the amino alcohol 16 against MCF-7 (11.9 mu M) and MO59J (10.0 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.037

文献信息

• Synthesis of three different galactose-based methacrylate monomers for the production of sugar-based polymers
  作者：Jessica S. Desport、Daniele Mantione、Mónica Moreno、Haritz Sardón、María J. Barandiaran、David Mecerreyes

  DOI：10.1016/j.carres.2016.06.008

  日期：2016.9

  the chemistry community. Glycidyl methacrylate (GMA) is an important building block for the synthesis of sugar based methacrylate monomers and polymers. Normally, glycidyl methacrylate shows some advantages such as reactivity against nucleophiles or milder synthetic conditions such as other reactive methacrylate monomers. However, condensation reactions of glycidyl methacrylate with for instance protected

  含合成糖的大分子糖醇共聚物引起了化学界的越来越多的关注。甲基丙烯酸缩水甘油酯（GMA）是糖基甲基丙烯酸酯单体和聚合物合成的重要组成部分。通常，甲基丙烯酸缩水甘油酯显示出一些优点，例如对亲核试剂的反应性或较温和的合成条件，例如其他反应性甲基丙烯酸酯单体。然而，由于两种可能途径之间的强竞争：环氧化物开环或酯交换，甲基丙烯酸缩水甘油酯与例如受保护的半乳糖单体的缩合反应导致两种产物的混合物。在本文中，我们提出了两种使用环氧开环反应合成区域特异性半乳糖基甲基丙烯酸酯单体的替代方法。在第一种替代路线中，首先将被保护的半乳糖氧化成酸，以使其对GMA的环氧化物更具反应性。在第二种方法中，首先用表氯醇处理被保护的糖，然后与甲基丙烯酸进行环氧开环反应，以产生GMA开环产物的类似物。使用常规的自由基聚合将这两种单体聚合，并与先前已知的半乳糖-甲基丙烯酸酯进行比较。相对于已知的半乳糖甲基丙烯酸酯聚合物，新聚合物显
• Surfactants Based on Bis‐Galactobenzimidazolones: Synthesis, Self‐Assembly and Ion Sensing Properties
  作者：L. Lakhrissi、N. Hassan、B. Lakhrissi、M. Massoui、E. M. Essassi、J. M. Ruso、C. Solans、C. Rodriguez‐ Abreu

  DOI：10.1007/s11743-011-1262-7

  日期：2011.10

  A series of new non‐ionic amphiphiles based on bis‐galactobenzimidazolones have been synthesized by grafting alkyl bis‐benzimidazolone units as hydrophobic tails on hydroxypropyloxygalacto‐pyranose moieties as hydrophilic heads. Their surface and self‐aggregation properties in water were evaluated. The compounds show very low critical micellar concentrations (CMCs) that decrease with increasing chain

  通过将烷基双苯并咪唑酮单元作为疏水尾部接枝在作为亲水头的羟丙基氧基半乳糖吡喃糖部分上，已经合成了一系列基于双半乳糖苯并咪唑酮的新型非离子两亲物。评估了它们在水中的表面和自聚集性能。这些化合物显示出非常低的临界胶束浓度（CMC），其随链长的增加而降低；界面上每个分子的最小面积的值（A min）遵循相同的趋势。合成的化合物还在水中形成一定范围的疏水尾长的六角形液晶。另一方面，新的两亲物表现出与苯并咪唑酮部分相关的特征性UV-Vis吸收和荧光发射带。荧光发射因其对苯并咪唑酮基团的强亲和力而被阳离子以一定程度的选择性猝灭，这显示出离子络合特性。因此，据报道，新的两亲物是自组装化学传感器的候选者。与胶束态相比，单体态的猝灭效率以及离子感测灵敏度更高。对于具有较短烷基链的化合物，荧光发射强度较高。
• Synthesis and screening of galactose-linked nitroimidazoles and triazoles against Mycobacterium tuberculosis
  作者：G. Mugunthan、Kuppala Ramakrishna、Dharmarajan Sriram、Perumal Yogeeswari、K.P. Ravindranathan Kartha

  DOI：10.1016/j.ejmech.2011.05.045

  日期：2011.9

  A series of galactose-linked nitroimidazoles/triazoles were synthesised and screened against Mycobacterium tuberculosis H(37)Rv. Preliminary results were promising with MIC values in the range 1.56-12.5 mu g/mL. Most importantly they are active under aerobic condition under which metronidazole is inactive. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis of galactopyranosyl amino alcohols as a new class of antitubercular and antifungal agents
  作者：Neetu Tewari、V.K. Tiwari、R.P. Tripathi、V. Chaturvedi、A. Srivastava、R. Srivastava、P.K. Shukla、A.K. Chaturvedi、A. Gaikwad、S. Sinha、B.S. Srivastava

  DOI：10.1016/j.bmcl.2003.11.020

  日期：2004.1

  The galactopyranosyl amino alcohols (3-16) were synthesised by regioselective oxirane ring opening of compound 2 with variety of amines and screened for antitubercular and antifungal activities. One of the compounds (16) showed potent activity against Mycobacterium tuberculosis H37 Rv in vitro and also displayed activity in MDR TB. The compound (16) was found to be superior to ethambutol clinically used anti TB drug in in vitro screen. (C) 2003 Elsevier Ltd. All rights reserved.
• Holme, Kevin R.; Hall, Laurance D., Canadian Journal of Chemistry, 1991, vol. 69, # 4, p. 585 - 589
  作者：Holme, Kevin R.、Hall, Laurance D.

  DOI：——

  日期：——