isopropyl-(α,β)-D-glucopyranoside | 124339-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl-(α,β)-D-glucopyranoside
• 英文别名: 1-O-isopropyl-glucopyranoside；isopropyl D-glucopyranoside；(2R,3S,4S,5R)-2-(hydroxymethyl)-6-propan-2-yloxyoxane-3,4,5-triol
• CAS: 124339-98-6
• 化学式: C₉H₁₈O₆
• 分子量: 222.238
• InChiKey: UOEFDXYUEPHESS-LOFWALOHSA-N

物化性质

• 沸点：
  395.0±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 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：

  isopropyl-(α,β)-D-glucopyranoside 在 碳酸氢钠 、 sodium chloride 作用下， 以 水 为溶剂， 以78%的产率得到isopropyl-(α,β)-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Process for selectively oxidizing primary hydroxyl groups of organic compounds, and resin containing adsorbed catalyst for use therein

  摘要：

  一种选择性氧化有机化合物中的主羟基的方法，包括将吸附有胺氧化物的树脂与含卤素化合物的电解氧化产物与具有主羟基的有机化合物反应。

  公开号：

  US06335464B1
• 作为产物：
  描述：

  异丙醇 、 4-硝基苯-Β-D-吡喃葡萄糖苷 在 Manihot esculenta Crantz linamarase 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.08h， 以60%的产率得到isopropyl-(α,β)-D-glucopyranoside
  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

• 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。
• Synthesis of alkyl α- and β-d-glucopyranoside-based chiral crown ethers and their application as enantioselective phase-transfer catalysts
  作者：Ádám Pálvölgyi、Zsolt Rapi、Olivér Ozohanics、Gábor Tóth、György Keglevich、Péter Bakó

  DOI：10.1007/s11164-017-3189-8

  日期：2018.3

  induction as phase-transfer catalysts in a few two-phase reactions. The catalytic effect of the lariat ethers with methoxy, ethoxy, and i-propoxy substituents on C-1 of the sugar unit in both α and β positions was compared. In liquid–liquid two-phase reactions, the nature and position of the substituents did not have much effect. The α-anomers were somewhat more efficient in terms of enantioselectivity than

  已经合成了与烷基4，6 - O-亚苄基-α-和β- d-葡萄糖吡喃糖苷退火的手性单氮杂-15-皇冠-5型套索状醚。这些大环在一些两相反应中作为相转移催化剂产生了明显的不对称诱导。套索醚与甲氧基，乙氧基，以及催化效果我-丙氧基取代基上C-1在两种α和β位置上的糖单元的进行比较。在液-液两相反应中，取代基的性质和位置没有太大影响。就对映选择性而言，α-异头物比β形式更有效。在不对称的Darzens缩合中，在反式的环氧化中-查尔酮，在β-硝基苯乙烯和乙酰胺基丙二酸的迈克尔加成反应中，以及2-亚苄基-1,3-茚满二酮与溴代丙二酸二乙酯的反应中，最大对映选择性分别达到73％，94％，78％和72％在基于吡喃葡萄糖苷的套索状醚作为催化剂的情况下。
• Monoesters of glycosides and a process for enzymatic preparation thereof
  申请人：Novo Nordisk A/S

  公开号：US05191071A1

  公开（公告）日：1993-03-02

  Compounds of the formula (R-COO).sub.n X-OR.sup.1, wherein R.sup.1 is optionally substituted alkyl, phenyl, or alkyl phenyl, n is 1, 2 or 3, X is a carbohydrate moiety, and R is optionally substituted alkyl, have superior effects as additives in detergents. These compounds can be prepared by esterification of glycosides using specific enzymes.

  公式为（R-COO）.sub.n X-OR.sup.1 的化合物，其中R.sup.1是可选择取代的烷基，苯基或烷基苯基，n为1、2或3，X是碳水化合物基团，R是可选择取代的烷基，作为洗涤剂添加剂具有优异效果。这些化合物可以通过使用特定酶对糖苷进行酯化反应制备。
• Fluorine-containing compounds and polymers derived therefrom
  申请人：——

  公开号：US20030109626A1

  公开（公告）日：2003-06-12

  Provided are fluorine-containing compounds, and polymers derived therefrom, for use in compositions used for treating textile substrates. Also provided are methods of making fluorine-containing compounds and polymers derived therefrom, compositions comprising the compounds and/or polymers of the present invention, methods of treating substrates, and the treated products derived therefrom.

  提供含氟化合物和由此衍生的聚合物，用于处理纺织物基材的组合物。还提供制备含氟化合物和由此衍生的聚合物的方法，包括本发明化合物和/或聚合物的组合物，处理基材的方法以及由此衍生的处理产品。
• Method for preparing organo glycosides
  申请人：A.E. STALEY MANUFACTURING COMPANY

  公开号：EP0099183A1

  公开（公告）日：1984-01-25

  Organo glycoside ethers are prepared by reacting saccharide containing compositions with alcohols of 3 or more carbon atoms in the presence of 2 or more moles of water for each aldose unit mole. The method is particularly effective for converting polysaccharides, such as starches to alkyl glycosides by means of a reaction media comprised of starch, an alkanol of at least 3 carbon atoms and at least one other alcohol-soluble organo co-solvent in the presence of an acid catalyst at elevated temperatures under pressure.

  有机糖苷醚是通过含糖组合物与 3 个或 3 个以上碳原子的醇在每个醛糖单元摩尔有 2 个或 2 个以上摩尔的水存在的情况下发生反应而制备的。该方法特别适用于将多糖（如淀粉）转化为烷基糖苷，其反应介质包括淀粉、至少 3 个碳原子的烷醇和至少一种其他醇溶性有机助溶剂，在酸催化剂存在下，在加温加压条件下进行。