methyl 6-O-stearoyl-α-D-glucopyranoside | 33535-00-1

• 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: methyl 6-O-stearoyl-α-D-glucopyranoside
• 英文别名: Methyl-6-O-stearoyl-α-D-glucopyranosid；Methyl 6-stearoyl-alpha-D-glucopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl octadecanoate
• CAS: 33535-00-1
• 化学式: C₂₅H₄₈O₇
• 分子量: 460.652
• InChiKey: WQAXDWGYHYPNIA-HFBCXCLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-O-stearoyl-α-D-glucopyranoside 、 己酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以82%的产率得到methyl 2,3,4-tri-O-hexanoyl-6-O-stearoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Stearoyl Glucopyranosides: Selective Synthesis, PASS Analysis, In Vitro Antimicrobial, and SAR Study

  摘要：

  DOI：

  10.21608/ejchem.2022.111831.5080
• 作为产物：
  描述：

  十八烷酰氯 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-O-stearoyl-α-D-glucopyranoside
  参考文献：
  名称：

  碳水化合物液晶：甲基-6-O-（n-酰基）-α-d-吡喃葡萄糖苷的合成与表征

  摘要：

  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，

  DOI：

  10.1016/j.chemphyslip.2010.11.007

文献信息

• 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。
• 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。
• 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.
• A New Highly Regioselective Reaction of Unprotected Sugars for Chemical Synthesis of Methyl-6-D-acyl-D-glycopyranosides by Mean of Chlorophosphoric Acid Diethyl Ester[(C₂H₅O)₂P(:O)Cl] as Condensing Reagent
  作者：Jie Xia、Yongzheng Hui

  DOI：10.1080/00397919608003614

  日期：1996.1

  A new methodology which allows the regioselective acylation of no protected methyl-D-glycopyranosides at the primary hydroxy group is described. Thus, a new synthetic procedure is presented to synthesize 6-acyl-methyl-glycopyranosides from unprotected glycopyranosides by means of (EtO)2P:OCl as condensing reagent.
• PLUSQUELLEC, DANIEL;BACZKO, KRYSTYNA, TETRAHEDRON LETT., 28,(1987) N 33, 3809-3812
  作者：PLUSQUELLEC, DANIEL、BACZKO, KRYSTYNA

  DOI：——

  日期：——