乙基 beta-D-吡喃葡萄糖苷 | 3198-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙基 beta-D-吡喃葡萄糖苷
• 中文别名: 乙基BETA-D-吡喃葡萄糖苷；乙基beta-D-吡喃葡萄糖苷；乙基 BETA-D-吡喃葡萄糖苷
• 英文名称: (2R,3R,4S,5S,6R)-2-Ethoxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• 英文别名: ethyl β-D-glucopyranoside；ethyl glucoside；ethyl β-D-glucoside；1-O-ethyl-β-D-glucopyranoside；ethyl beta-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-ethoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 3198-49-0；30285-48-4
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: WYUFTYLVLQZQNH-JAJWTYFOSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  98-100°C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 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：

  乙基 beta-D-吡喃葡萄糖苷 在 almond meal 作用下， 以 水 为溶剂， 反应 336.0h， 生成 丙基 BETA-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

  摘要：

  An array of ten beta-D-glueopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl beta-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl beta-D-glucoside was found to have significant surface activity as well.

  DOI：

  10.1016/s1872-2067(11)60333-1
• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 水 作用下， 以 水 、 乙腈 为溶剂， 反应 168.0h， 生成 乙基 beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

  摘要：

  An array of ten beta-D-glueopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl beta-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl beta-D-glucoside was found to have significant surface activity as well.

  DOI：

  10.1016/s1872-2067(11)60333-1
• 作为试剂：
  描述：

  乙基 D-吡喃葡萄糖苷 、 月桂酸 、 在 fatty acid 、 乙基 beta-D-吡喃葡萄糖苷 、 mixture 、 diesters 作用下， 70.0~105.0 ℃ 、533.29 Pa 条件下， 反应 23.0h， 以yielding 96% (1050 g) of crude product along with 2% ethyl D-glucoside and 2% of a mixture of diesters (HPLC analysis)的产率得到ethyl 6-O-dodecanoyl-D-glucopyranoside
  参考文献：
  名称：

  Monoesters of glycosides and a process for enzymatic preparation thereof

  摘要：

  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。

  公开号：

  US05191071A1

文献信息

• Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry
  作者：Yasuhiro Meguro、Masato Noguchi、Gefei Li、Shin-ichiro Shoda

  DOI：10.1021/acs.orglett.7b03400

  日期：2018.1.5

  thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named “glycosyl Bunte salts” after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water–acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation

  S-糖基硫代硫酸盐已被发现是糖化学中的一类新型合成中间体，以19世纪德国化学家汉斯·邦特（Hans Bunte）的名字命名为“糖基邦特盐”。通过在水-乙腈混合溶剂中使用甲am型脱水剂将未保护的糖和硫代硫酸钠直接缩合来完成合成。通过向其他糖基化合物如1-硫糖，糖基二硫化物，1，6-脱水糖和O-糖苷的转化反应证明了糖基邦特盐的应用。
• 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。
• A new phenolic metabolite, involutone, isolated from the mushroom <i>Paxillus involutus</i>
  作者：Róza Antkowiak、Wieslaw Z Antkowiak、Izabela Banczyk、Lucyna Mikolajczyk

  DOI：10.1139/v02-194

  日期：2003.1.1

  as well as methyl, ethyl, or n-butyl-β-D-glucopyranosides, and methyl, ethyl, or n-butyl linoleates, depending in both cases on the alcohol used in the extraction, were also isolated in a pure state from the mushroom.Key words: Paxillus involutus, Brown Roll-rim, metabolite isolation, structure study, quaternary hydroxycyclopentanedione, NMR of mushroom pigments, glucosides and linoleates, enzymic glucosylation

  一种新的光学活性代谢物 involutone，在新鲜收集的 Paxillus involutus 的甲醇、乙醇或正丁醇提取物中被发现。根据光谱和化学性质证明该化合物的结构为 5-(3,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2-hydroxy-4-cyclopenten-1,3-dione内卷酮及其四乙酰基衍生物。此外，许多已知结构的化合物，例如亚油酸和巴豆酸、甘露醇、麦角甾醇、内卷素，以及甲基、乙基或正丁基-β-D-吡喃葡萄糖苷，以及甲基、乙基或正丁基亚油酸酯，在这两种情况下都取决于提取中使用的酒精，也从蘑菇中以纯状态分离出来。 关键词： 渐开线芽孢杆菌，棕卷缘，代谢物分离，结构研究，季羟基环戊二酮，蘑菇色素的核磁共振，
• POLYMER STABILIZER
  申请人：KIMURA Yoshikazu

  公开号：US20100179253A1

  公开（公告）日：2010-07-15

  A polymer stabilizer comprising the following alkoxy compound: the alkoxy compound: a compound obtained by alkoxylating at least one hydroxyl group contained in a compound of the following formula (1) containing one formyl group or carbonyl group and (n− 1 ) hydroxyl groups in the molecule with an alkyl group having 1 to 12 carbon atoms: C n H 2n O n (1) (wherein, n represents an integer of 3 or more).

  一种聚合物稳定剂，包含以下烷氧基化合物：所述烷氧基化合物是通过将含有以下通式（1）中的一个甲酰基或羰基以及分子中（n-1）个羟基的化合物中的至少一个羟基进行烷氧基化而得到的化合物，其中烷基团含有1至12个碳原子：CnH2nOn（1）（其中，n代表3或以上的整数）。
• Regioselective acylation of carbohydrate derivatives using lipases leading to a facile two-step procedure for the separation of some α- and β-glucopyranosides and galactopyranosides
  作者：Pedro M.L Gonçalves、Stanley M Roberts、Peter W.H Wan

  DOI：10.1016/j.tet.2003.11.035

  日期：2004.1

  The resolution of α- and β-anomers of glucopyranosides and galactopyranosides was achieved via enzyme-catalysed regioselective acylation. This two-step procedure to prepare pure α- and β-anomers of glycopyranosides would be most useful for the cases where glycosidases are not available or expensive to purchase. From a synthetic viewpoint, the regioselective acylation of glycopyranosides provides access

  葡萄糖吡喃糖苷和吡喃半乳糖苷的α-和β-端基异构体的拆分是通过酶催化的区域选择性酰化作用实现的。这种制备糖吡喃糖苷的纯α-和β-端基异构体的两步程序对于糖苷酶不可用或购买价格昂贵的情况将是最有用的。从合成的观点来看，糖吡喃糖苷的区域选择性酰化作用提供了具有明确定义的取代模式的单酯和二酯的途径。