6-O-dodecanoyl-methyl-α-D-glucopyranoside | 20869-08-3

• 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-dodecanoyl-methyl-α-D-glucopyranoside
• 英文别名: Methyl 6-O-dodecanoyl-α-D-glucopyranoside；methyl 6-O-lauroyl-α-D-glucopyranoside；Methyl-6-O-lauroyl-α-D-glucopyranosid；α-Methyl-D-glucopyranosid-6-laurinat；methyl 6-O-dodecanoyl-alpha-d-glucopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl dodecanoate
• CAS: 20869-08-3
• 化学式: C₁₉H₃₆O₇
• 分子量: 376.491
• InChiKey: RWBZTJOMOZRUCK-FTWQHDNSSA-N

物化性质

• 熔点：
  70.30 °C
• 沸点：
  501.1±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  potassium;[(2R,3S,4R,5R,6S)-2-(dodecanoyloxymethyl)-4,5-dihydroxy-6-methoxyoxan-3-yl] sulfate 在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 6-O-dodecanoyl-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Regiospecific Synthesis of New Methyl Sulfoglucopyranoside-Based Surfactants: Nucleophilic Displacement of a Cyclic Sulfate

  摘要：

  本文介绍了一种新型阴离子和两性甲基δ-d-吡喃葡萄糖苷表面活性剂的两步特异性合成方法。甲基 δ±-d-吡喃葡萄糖苷与亚硫酰氯反应，然后氧化生成的亚硫酸盐，就能以高产率得到相应的甲基 δ±-d-吡喃葡萄糖苷 4,6 环硫酸盐。用不同的脂肪酸和胺对这种环状硫酸酯进行亲核置换，可以得到相应的 6-O-酰基或 6-氨基-6-脱氧-4-磺酸基吡喃葡萄糖苷，产率非常高。这些新合成的磺基吡喃葡萄糖苷表面活性剂显示出较低的临界胶束浓度（CMC）值。

  DOI：

  10.1055/s-1999-3432

文献信息

• A highly selective enzyme-catalysed esterification of simple glucosides
  作者：Fredrik Björkling、Sven Erik Godtfredsen、Ole Kirk

  DOI：10.1039/c39890000934

  日期：——

  Regioselective 6-O-esterification of alkyl glucosides with long chain fatty acids, yielding more than 95% of 6-O-monoesters, can be achieved using lipases as catalysts in a solvent-free process.

  使用脂肪酶作为催化剂，在无溶剂的过程中，烷基糖苷与长链脂肪酸的区域选择性6- O-酯化反应可产生超过95％的6- O-单酯。
• Sugar chemistry without protecting groups-III. A facile chemical synthesis of 6-O-acyl-D-glycopyranoses and methyl-6-O-acyl-d-glycopyranosides.
  作者：Krystyna Baczko、Daniel Plusquellec

  DOI：10.1016/s0040-4020(01)80906-6

  日期：——

  Regioselective acylation of non protected glycopyranosides was performed using 3- acylthiazolidine-2-thiones 1 and the novel 3-acyl-5-methyl-1,3,4-thiadiazole-2(3H)-thiones 2 as the acylating reagents, yielding 6-O-acylated derivatives in high yields. Acylation of free α-D-glucose and α-D-galactose using the same conditions lead to the 6-O-acylglycoses. This reaction is compared with our previous synthesis

  使用3-酰基噻唑烷-2-硫酮1和新型3-酰基-5-甲基-1,3,4-噻二唑-2（3H）-硫酮2作为酰化剂，对未保护的吡喃葡萄糖苷进行区域选择性酰化，得到6 -O-酰化衍生物的产率高。在相同条件下将游离α-D-葡萄糖和α-D-半乳糖酰化，得到6-O-酰基糖。将该反应与我们先前由PD-葡萄糖合成的1-O-酰基-β-D-葡萄糖进行了比较。
• 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。
• Carbohydrate liquid crystals: Synthesis and characterisation of the methyl-6-O-(n-acyl)-α-d-glucopyranosides
  作者：Andrew G. Cook、James L. Wardell、Corrie T. Imrie

  DOI：10.1016/j.chemphyslip.2010.11.007

  日期：2011.2

  marked change at the melting point but apparently no change at the smectic A-isotropic transition. This observation is interpreted in terms of Goodby's model for the smectic A phase in which the carbohydrate moieties are located at the centre of the smectic bilayer and assuming that hydrogen bonded aggregates persist into the isotropic phase. Within this framework, the unusually low values of the entropy

  甲基-6-O-（n-酰基）-α- d的七个成员已经合成了β-吡喃葡萄糖苷并确定了它们的过渡性质。十一烷酰基和十八烷酰基成员不表现出液晶性，而链长在十二烷酰基和十六烷酰基之间的成员表现出单向性近晶A相。可变温度红外光谱显示，系统内的氢键在熔点处显示出明显的变化，但在近晶A-各向同性转变时显然没有变化。该观察结果是根据针对近晶A相的古德模型来解释的，其中碳水化合物部分位于近晶双层的中心，并假设氢键合的聚集体持续存在于各向同性相中。在这个框架内，
• Sugar chemistry without protecting groups: a novel regioselective synthesis of 6-O-acyl-D-glucopyranoses and methyl-6-O-acyl-α--glucopyranosides
  作者：Daniel Plusquellec、Krystyna Baczko

  DOI：10.1016/s0040-4039(00)96390-1

  日期：1987.1

  hydroxyl groups of α--glucose and methyl-α--glucoside were selectively esterified by treating the free sugars with -acylthiazolidine-2-thiones, thus affording respectively 6--acyl--glucopyranoses and methyl-6--acyl-α--glucopyranosides in high yields. This new reaction is compared with our previous synthesis of 1--acyl-β--glucopyranoses from β--glucose and interpreted in terms of anomeric effect.

  通过用-酰基噻唑烷-2-硫酮处理游离糖，选择性地酯化α-葡萄糖和甲基-α-葡萄糖苷的伯羟基，分别得到6-酰基-葡萄糖吡喃糖和甲基-6-酰基- α--吡喃葡萄糖苷的产率高。将该新反应与我们先前从β-葡萄糖合成1-酰基-β-葡萄糖吡喃糖进行了比较，并根据异头作用进行了解释。