methyl 6-O-lauroyl-α-D-mannopyranoside | 135363-38-1

• 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-lauroyl-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl dodecanoate
• CAS: 135363-38-1
• 化学式: C₁₉H₃₆O₇
• 分子量: 376.491
• InChiKey: RWBZTJOMOZRUCK-IQRFUGTFSA-N

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

• 作为反应物：
  描述：

  methyl 6-O-lauroyl-α-D-mannopyranoside 、 棕榈酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以76%的产率得到methyl 6-O-lauroyl-2,3,4-tri-O-palmitoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis, characterization, ADMET, PASS predication, and antimicrobial study of 6-O-lauroyl mannopyranosides

  摘要：

  Methyl alpha-D-mannopyranoside (MDM, 1) was subjected to direct unimolar lauroylation in pyridine at low temperature (0-20 degrees C) with lauroyl chloride. It showed regioselectivity at C-6 position and furnished 6-O-lauroyl-alpha-D-mannopyranoside 3 in 59% yield. For structural elucidation as well as to get newer mannopyranosides of biological importance compound 3 was converted to eight newer 2,3,4-tri-O-acylates 4-11 in good yields. PASS predication and antimicrobial studies showed that these compounds possess better anti-fungal activities than that of antibacterial functionalities. ADMET, PASS prediction and antimicrobial study have performed to evaluate the pharmacokinetic and microbial properties of MDM esters. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.05.102
• 作为产物：
  描述：

  月桂酰氯 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 6-O-lauroyl-α-D-mannopyranoside
  参考文献：
  名称：

  没有保护基的糖化学-III。6-O-酰基-D-甘露糖和甲基-6-O-酰基-d-吡喃糖苷的简便化学合成。

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(01)80906-6

文献信息

• A Comparison of the Antibacterial Efficacy of Carbohydrate Lipid-like (Thio)Ether, Sulfone, and Ester Derivatives against Paenibacillus larvae
  作者：Veronika Šamšulová、Mária Šedivá、Juraj Kóňa、Jaroslav Klaudiny、Monika Poláková

  DOI：10.3390/molecules28062516

  日期：——

  than their decylated analogs. Thioglycosides were more efficient than glycosides and sulfones. The activity of the 6-O-ether derivatives was higher than that of their ester counterparts. Seven derivatives with dodecyl chain linked (thio)glycosidically or etherically at C-6 showed high efficacy against both P. larvae strains (MICs ranged from 12.5 μM to 50 μM). Their efficacies were similar or much higher

  类芽孢杆菌幼虫是美洲臭虫 (AFB) 的病原体，AFB 是影响蜜蜂幼虫和蛹发育的最严重的细菌性疾病。在这项研究中，评估了从具有 C10 或 C12 烷基链的 d-甘露糖、d-葡萄糖和 d-半乳糖衍生的 24 种（硫代）糖苷、糖基砜、6-O-酯和醚的文库的抗菌功效针对两种 P. 幼虫菌株。以最小抑制浓度 (MIC) 确定的受试化合物的功效差异很大。通常，发现十二烷基衍生物比它们的癸基化类似物更有效。硫苷比苷和砜更有效。6-O-醚衍生物的活性高于它们的酯对应物。在 C-6 处具有十二烷基链（硫代）糖苷或醚连接的七种衍生物显示出对两种 P. 幼虫菌株的高效（MIC 范围从 12.5 μM 到 50 μM）。它们的功效与已知对 P. larvae-lauric acid、monolaurin 和蜜蜂幼虫食物成分、10-hydroxy-2-decenoic acid 和 sebacic acid（MIC
• 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。
• Synthesis, characterization, ADMET, PASS predication, and antimicrobial study of 6-O-lauroyl mannopyranosides
  作者：Mohammed M. Matin、Md M.H. Bhuiyan、Emranul Kabir、Abul F.M. Sanaullah、Md A. Rahman、Md E. Hossain、Monir Uzzaman

  DOI：10.1016/j.molstruc.2019.05.102

  日期：2019.11

  Methyl alpha-D-mannopyranoside (MDM, 1) was subjected to direct unimolar lauroylation in pyridine at low temperature (0-20 degrees C) with lauroyl chloride. It showed regioselectivity at C-6 position and furnished 6-O-lauroyl-alpha-D-mannopyranoside 3 in 59% yield. For structural elucidation as well as to get newer mannopyranosides of biological importance compound 3 was converted to eight newer 2,3,4-tri-O-acylates 4-11 in good yields. PASS predication and antimicrobial studies showed that these compounds possess better anti-fungal activities than that of antibacterial functionalities. ADMET, PASS prediction and antimicrobial study have performed to evaluate the pharmacokinetic and microbial properties of MDM esters. (C) 2019 Elsevier B.V. All rights reserved.