丁基 D-葡糖苷 | 31387-97-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 丁基 D-葡糖苷
• 中文别名: 丁基D-葡糖苷
• 英文名称: n-butyl D-glucoside
• 英文别名: butyl D-glucopyranoside；butyl glycoside；α-butylglucoside；n-butyl glucoside；n-butylglucoside；butyl glucoside；Butyl D-glucoside；(3R,4S,5S,6R)-2-butoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 31387-97-0
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: BZANQLIRVMZFOS-ZKZCYXTQSA-N

物化性质

• 熔点：
  66-67 °C
• 沸点：
  412.0±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丁基 D-葡糖苷 在 sodium 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 butyl-α-D-glucopyranoside
  参考文献：
  名称：

  烷基葡糖苷的双子表面活性剂

  摘要：

  通过简单的方法，从d-葡萄糖开始合成1，5-双-[6- O-（正丁基α- d-吡喃葡萄糖苷）]戊二酸酯7。烷基葡糖苷的异头物混合物通过其过乙酸酯的快速色谱法分离。描述了中性条件下的去三苯甲基化。这是非离子双子表面活性剂的第一个例子，其中烷基葡糖苷通过C-6处的间隔基连接。

  DOI：

  10.1016/s0040-4039(97)00817-4
• 作为产物：
  描述：

  4-硝基苯-Β-D-吡喃葡萄糖苷 、 正丁醇 在 Dalbergia cochinchinensis Pierre dalcochinase N₁₈₉F mutant 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.08h， 以96%的产率得到丁基 D-葡糖苷
  参考文献：
  名称：

  Substrate specificity in hydrolysis and transglucosylation by family 1 β-glucosidases from cassava and Thai rosewood

  摘要：

  Thai rosewood (Dalbergia cochinchinensis Pierre) dalcochinase and cassava (Manihot esculenta Crantz) linamarase are glycoside hydrolase family 1 beta-glucosidases with 47% amino acid sequence identity. Each enzyme can hydrolyze its natural substrate, dalcochinin-8'-O-beta-D-glucoside and linamarin, respectively, but not the natural substrate of the other enzyme. Linamarase can transfer glucose to primary, secondary and tertiary alcohols with high efficiency, while dalcochinase can transglucosylate primary and secondary alcohols at moderate levels. In this study, eight amino acid residues in the aglycone binding pocket of dalcochinase were individually replaced with the corresponding residues of linamarase, in order to identify residues that may account for their catalytic differences. The residues 1185 and V255 of dalcochinase appeared important for its substrate specificity, with their respective mutations resulting in 24- and 12-fold reductions in K-cat/K-m for the hydrolysis of dalcochinin-8'-O-beta-D-glucoside. Transglucosylation activity was improved when 1185, N189 and V255 of dalcochinase were replaced with A201, F205 and F271 of linamarase, respectively, suggesting these residues support transglucosylation in linamarase. Among these three mutants, only the N189F mutant showed significant increases in the rate constants for the reactivation of trapped glucosyl-enzyme intermediates by all alcohols. Together, our results suggest that both hydrophobicity and geometry are important determinants for substrate specificity in hydrolysis and transglucosylation by these family 1 beta-glucosidases. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.09.003

文献信息

• Transformation of Cellulose into Biodegradable Alkyl Glycosides by Following Two Different Chemical Routes
  作者：Nicolas Villandier、Avelino Corma

  DOI：10.1002/cssc.201000371

  日期：2011.4.18

  cellulose into long‐chain alkyl glycoside surfactants has been carried out following two different routes: (1) Direct transformation of cellulose to butyl‐, hexyl‐, octyl‐, decyl‐ and dodecyl‐α,β‐glycosides in an ionic liquid media and Amberlyst‐15Dry as catalysts, with mass yield of up to 82 %; and (2) two steps reaction with transformation of cellulose into methyl glucosides, with a procedure described

  纤维素向长链烷基糖苷表面活性剂的转化已通过以下两种不同的途径进行：（1）纤维素在离子性离子中直接转化为丁基，己基，辛基，癸基和十二烷基-β-糖苷。液体介质和Amberlyst-15Dry作为催化剂，质量产率高达82％；（2）两步反应，按照Zhang等人的描述，将纤维素转化为甲基葡糖苷，然后在Amberlyst-15Dry存在下，用1-辛醇和1-癸醇进行缩醛化。使用1-辛醇对纤维素进行直接转化的动力学研究表明，在费歇尔糖苷化过程中，纤维素的解聚反应仍在继续。由于醇的亲脂性的增加（其减少了与碳水化合物的接触），增加了醇的链长会降低总体反应速率。最后，测试了几种酸催化剂，使用Amberlyst-15Dry获得了最佳结果。
• Montmorillonite K-10 as a Reusable Catalyst for Fischer Type of Glycosylation under Microwave Irradiation
  作者：Dipak K. Roy、Manobjyoti Bordoloi

  DOI：10.1080/07328300802107437

  日期：2008.7

  Montmorillonite K10 catalyzed Fischer type glycosylation was studied for various monosacharides with different alcohols under microwave irradiation. The method was found to be efficient, economic, simple and time saving and the catalyst montmorillonite K-10 was reused three times without loss of catalytic activity and anomeric selectivity. With glycerol, the method gave products glycosylated at primary

  在微波辐射下，研究了蒙脱石K10催化的费歇尔型糖基化反应，研究了用不同醇制得的各种单糖。发现该方法是有效，经济，简单和省时的，并且催化剂蒙脱石K-10可重复使用三次，而不会损失催化活性和端基异构体选择性。对于甘油，该方法仅产生在伯醇处糖基化的产物。
• Acid-Assisted Ball Milling of Cellulose as an Efficient Pretreatment Process for the Production of Butyl Glycosides
  作者：Florent Boissou、Nassim Sayoud、Karine De Oliveira Vigier、Abdellatif Barakat、Sinisa Marinkovic、Boris Estrine、François Jérôme

  DOI：10.1002/cssc.201500700

  日期：2015.10

  Ball milling of cellulose in the presence of a catalytic amount of H2SO4 was found to be a promising pre‐treatment process to produce butyl glycosides in high yields. Conversely to the case of water, n‐butanol has only a slight effect on the recrystallization of ball‐milled cellulose. As a result, thorough depolymerization of cellulose prior the glycosylation step is no longer required, which is a

  人们发现，在催化量的H 2 SO 4的存在下，球磨纤维素是一种有前途的预处理方法，可以高产率地生产丁基糖苷。与水相反，正丁醇对球磨纤维素的重结晶影响很小。结果，不再需要在糖基化步骤之前对纤维素进行彻底的解聚，这是关于能量消耗的关键方面。该方法成功地转移到麦秆上，从麦秆中可得到高产的丁基糖苷和木糖苷。丁基糖苷和木糖苷是重要的化学品，因为它们既可以用作水溶助长剂，又可以用作生产有价值的两亲烷基糖苷的中间体。
• 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。
• Surface active compounds and a process for their preparation
  申请人：Cerestar Holding BV

  公开号：US04959459A1

  公开（公告）日：1990-09-25

  6-C.sub.8 to C.sub.22 acyl-1-C.sub.3 to C.sub.12 alkylglucosides are a new group of surface active compounds useful in particular as emulsifiers in cosmetics, pharmaceutical compositions and foodstuffs. They are prepared by reacting a 1-C.sub.3 to C.sub.12 alkyl glucoside with a C.sub.8 to C.sub.22 fatty acid in the presence of a lipolytic enzyme and in a reaction medium containing at most 30% and preferably 0.01 to 5% water.

  6-C.sub.8至C.sub.22烷酰-1-C.sub.3至C.sub.12烷基葡萄糖苷是一类新型表面活性化合物，特别适用于化妆品、药品和食品中的乳化剂。它们是通过将1-C.sub.3至C.sub.12烷基葡萄糖苷与C.sub.8至C.sub.22脂肪酸在存在脂肪酶的情况下进行反应，并在含有最多30%和最好为0.01至5%水的反应介质中制备的。

表征谱图