6-O-(9Z)-octadecenoyl-methyl-α-D-glucopyranoside | 133211-19-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6-O-(9Z)-octadecenoyl-methyl-α-D-glucopyranoside
• 英文别名: methyl 6-O-oleoyl-α-D-glucopyranoside；W5RQ55ZQ2J；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl (Z)-octadec-9-enoate
• CAS: 133211-19-5
• 化学式: C₂₅H₄₆O₇
• 分子量: 458.636
• InChiKey: HLPLRASSAVUVIN-WXZIMHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  S-oleoyl-p-nitrothiophenol 、 alpha-甲基葡萄糖甙 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以57%的产率得到6-O-(9Z)-octadecenoyl-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  A New Highly Regioselective Reaction of Unprotected Sugars for Chemical Synthesis of 6-Acyl-D-Glycopyranosides

  摘要：

  New methodologies developed to synthesize 6-acyl-D-glycopyranosides are described. Thus, regioselective acylation of non protectedglycopyranosides was performed using acyl-p-nitrothiophenol esters and acyl-2,4-dinitrophenol esters as the acylating reagents, yielding 6-acylated derivatives in high yields.

  DOI：

  10.1080/00397919508011779

文献信息

• Ionic liquid-coated immobilized lipase for the synthesis of methylglucose fatty acid esters
  作者：Julien Mutschler、Thierry Rausis、Jean-Marc Bourgeois、Christèle Bastian、Daniel Zufferey、Isabelle Vanessa Mohrenz、Fabian Fischer

  DOI：10.1039/b916016g

  日期：——

  A homologous series of biosurfactants has been synthesized by a novel sustainable biotransformation technique and compared with three other enzymatic processes. 6-O-Alkanoyl-methyl-α-D-glucopyranosides were obtained by lipase mediated esterification of methyl-α-D-glucopyranoside with capric acid C10:0, lauric acid C12:0, myristic acid C14:0, palmitic acid C16:0, and oleic acid C18:1. Solvent free transformations were compared with the use of ionic liquids and organic solvents. The lipase from Candida antarctica B, immobilized on macroporous acrylic acid beads (Novozyme 435), was employed either untreated or coated with small amounts of ionic liquids. This resulted in superior efficiencies (80%) with 1-butyl-4-methylpyridine hexafluorophosphate [4bmpy][PF6] and broader substrate tolerance in comparison to solvent free transformation. The results show a positive correlation with increasing polarity of the ionic liquids used as liquid film-coating, which was in opposition to the use of the same ionic liquid as solvent. The analysis of the ionic liquid film coated catalyst carriers was performed by optical and scanning electron microscopy (SEM).

  一系列同源生物表面活性剂通过一种新颖的可持续生物转化技术合成，并与三种其他酶促过程进行了比较。通过脂肪酶催化将甲基-α-D-葡萄糖苷与癸酸C10:0、月桂酸C12:0、肉豆蔻酸C14:0、棕榈酸C16:0和油酸C18:1进行酯化，得到了6-O-烃酰基-甲基-α-D-葡萄糖苷。无溶剂转化与使用离子液体和有机溶剂进行了比较。采用从南极假单胞菌B中提取的脂肪酶，负载于多孔丙烯酸珠（Novozyme 435）上，使用未处理或涂覆少量离子液体的方式。这导致使用1-丁基-4-甲基吡啶六氟磷酸盐[4bmpy][PF6]时，反应效率达到了80%，并且相较于无溶剂转化具有更广泛的基质耐受性。结果表明，使用的离子液体作为液膜涂层时，其极性增加与效率之间存在正相关，而作为溶剂使用时则相反。通过光学显微镜和扫描电子显微镜（SEM）对涂覆离子液膜的催化剂载体进行了分析。
• A New Highly Regioselective Reaction of Unprotected Sugars for Chemical Synthesis of 6-Acyl-D-Glycopyranosides
  作者：Jie Xia、Yongzheng Hui

  DOI：10.1080/00397919508011779

  日期：1995.8

  New methodologies developed to synthesize 6-acyl-D-glycopyranosides are described. Thus, regioselective acylation of non protectedglycopyranosides was performed using acyl-p-nitrothiophenol esters and acyl-2,4-dinitrophenol esters as the acylating reagents, yielding 6-acylated derivatives in high yields.