乙基2,3-O-异亚丙基-beta-D-呋喃核糖苷 | 704916-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙基2,3-O-异亚丙基-beta-D-呋喃核糖苷
• 中文别名: 乙酮,2-氯-1-(3,4-二氨基苯基)-
• 英文名称: ethyl 2,3-O-isopropylidene-β-D-ribofuranoside
• 英文别名: [(3aR,4R,6R,6aR)-4-ethoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 704916-06-3
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: KITJEQXHHXMTOT-FNCVBFRFSA-N

物化性质

• 沸点：
  302.9±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙基2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 正丁基锂 、 samarium diiodide 、 dipyrrolidinomethylaminophosphoric acid triamide 、 sodium hydride 、 叔丁醇 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.33h， 生成 1-O-ethyl-5-O-n-butyl-2,3-O-isopropylidene-β-d-ribofuranose
  参考文献：
  名称：

  二吡咯烷基甲基氨基磷酸三酰胺（DPMPA）作为二碘化sa介导的烷基卤和芳基卤化物还原的活化剂

  摘要：

  使用dipyrrolidinomethylaminophosphoric磷酰三胺（DPMPA的共轭碱的-被报告为的二碘化钐的活化剂）。该氨基磷酸酯已被证明是非常有效的配体，可以有效，低温地还原烷基和芳基氯化物。还报道了卤代烯基萘的还原环化。

  DOI：

  10.1016/j.tet.2013.02.025
• 作为产物：
  描述：

  乙醇 、 卡培他滨杂质25 、 丙酮 在 硫酸 作用下， 反应 48.0h， 以76%的产率得到乙基2,3-O-异亚丙基-beta-D-呋喃核糖苷
  参考文献：
  名称：

  核糖基离子液体的结构性质关系

  摘要：

  这项工作的作者成功地合成了多种新的基于核糖的离子液体，在碳水化合物的不同位置使用不同的保护基（甲基，乙基，烯丙基和苄基），以及不同的季铵化N-杂环和不同阴离子。碳水化合物基离子液体（CHIL）的这些一致的变化使得能够进行广泛的热性质结构-性质关系研究，从而使作者能够证明现有的趋势并发现分解温度与CHILs结构之间的相关性。

  DOI：

  10.1016/j.molliq.2020.115167

文献信息

• Method of fluorination
  申请人：Hara Shoji

  公开号：US20060014972A1

  公开（公告）日：2006-01-19

  A method of fluorination comprising reacting monosaccharides, oligosaccharides, polysaccharides, composite saccharides formed by bonding of these saccharides with proteins and lipids and saccharides having polyalcohols, aldehydes, ketones and acids of the polyalcohols, and derivatives and condensates of these compounds with a fluorinating agent represented by general formula (I) thermally or under irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region. In accordance with the method, the fluorination at a selected position can be conducted safely at a temperature in the range of 150 to 200° C. where the reaction is difficult in accordance with conventional methods. The above method comprising the irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region can be applied to substrates other than saccharides. When a complex compound comprising HF and a base is reacted under irradiation with microwave, fluorination at a specific position which is difficult in accordance with conventional methods proceeds highly selectively, efficiently in a short time and safely.

  一种氟化方法，包括通过热力学或微波辐射或波长在微波区域附近的电磁波与一种通式为(I)的氟化试剂反应，反应单糖，低聚糖，多糖，由这些糖与蛋白质和脂质结合形成的复合糖和具有多元醇，醛，酮和多元醇的酸以及这些化合物的衍生物和缩聚物。根据该方法，可以在150到200°C的温度范围内安全地进行选择性的氟化反应，而在传统方法中难以进行。上述方法包括使用微波或波长在微波区域附近的电磁波辐射，可应用于除糖类以外的基质。当HF和碱组成的复合物在微波辐射下反应时，难以在传统方法中进行的特定位置的氟化反应高度选择性，高效地在短时间内安全进行。
• Characteristic ¹H NMR spectra of β-<scp>d</scp>-ribofuranosides and ribonucleosides: factors driving furanose ring conformations
  作者：Dominik Walczak、Artur Sikorski、Daria Grzywacz、Andrzej Nowacki、Beata Liberek

  DOI：10.1039/d2ra04274f

  日期：——

  studied in terms of their conformational preferences. Based on the 1H NMR spectra, DFT calculations, and X-ray analysis the E0-like and E4-like conformations adopted by these furanosides are identified. The 3E-like and 2E-like conformations are assigned to ribonucleosides without the 2,3-O-isopropylidene group. The studies are supported by analysis of the structural data of β-D-ribofuranosides and

  合成了一系列β- D-呋喃核苷和2,3- O-异亚丙基环稠合核糖核苷，并研究了它们的构象偏好。基于1 H NMR 谱、DFT 计算和 X 射线分析，鉴定了这些呋喃糖苷采用的E 0样和E 4样构象。 3 E样和2 E样构象被指定为不带 2,3- O-异丙叉基团的核糖核苷。这些研究得到了剑桥晶体数据中心 (CCDC) 数据库中 β- D-呋喃核苷和核糖核苷结构数据分析的支持。最后，指出了影响β- D-核糖构型呋喃糖环构象偏好的因素。这些是2-OH和3-OH基团的不利黄道方向、糖苷配基和末端羟甲基的1,3-赝双轴相互作用以及内异头效应。还证明外型异头效应作用于β- D-呋喃核苷。
• METHOD OF FLUORINATION
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：EP1568703A1

  公开（公告）日：2005-08-31

  A method of fluorination comprising reacting monosaccharides, oligosaccharides, polysaccharides, composite saccharides formed by bonding of these saccharides with proteins and lipids and saccharides having polyalcohols, aldehydes, ketones and acids of the polyalcohols, and derivatives and condensates of these compounds with a fluorinating agent represented by general formula (I) thermally or under irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region. In accordance with the method, the fluorination at a selected position can be conducted safely at a temperature in the range of 150 to 200°C where the reaction is difficult in accordance with conventional methods. The above method comprising the irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region can be applied to substrates other than saccharides. When a complex compound comprising HF and a base is reacted under irradiation with microwave, fluorination at a specific position which is difficult in accordance with conventional methods proceeds highly selectively, efficiently in a short time and safely.

  一种氟化方法，包括使单糖、低聚糖、多糖、这些糖与蛋白质和脂类结合形成的复合糖、具有多元醇、多元醇的醛、酮和酸的糖、以及这些化合物的衍生物和缩合物与通式(I)代表的氟化剂进行热反应或在微波或波长在微波区域附近的电磁波照射下进行反应。根据该方法，可在 150 至 200°C 的温度范围内安全地进行所选位置的氟化反应，而在此温度范围内，根据传统方法很难进行反应。上述方法包括用微波或波长在微波区域附近的电磁波进行辐照，可用于糖类以外的基质。在微波辐照下反应由氟化氢和碱组成的复杂化合物时，在传统方法难以进行的特定位置上的氟化反应可在短时间内高效、安全地进行，且选择性高。
• METHOD OF FLUORINATION BY MICROWAVES
  申请人：Mitsubishi Gas Chemical Company, Inc.

  公开号：EP2189466A2

  公开（公告）日：2010-05-26

  A method of fluorination which comprises fluorinating a substrate by bringing the substrate and a fluorinating agent into reaction with each other under irradiation with at least one of microwave and electromagnetic wave having a wavelength around a microwave region; wherein the substrate is selected from the group consisting of monohydroxy alcohol; polyol having a plurality of hydroxyl groups; thiol; a compound having a carbonyl group or carboxyl group; an aromatic compound exhibiting an increased nucleophilicity due to the presence of an electron-attracting group; aromatic diazonium salt; oligosaccharide and polysaccharide; hydrocarbon having a cage shape; and epoxide; and the fluorinating agent is represented by general formula (I): wherein Y represents nitrogen atom or phosphorus atom, R0, R1 and R2 represent hydrogen atom or an alkyl or aryl group which may have substituents, the atom and the groups represented by R0, R1 and R2 may be the same with or different from each other, and two or three of the groups represented by R0, R1, and R2 may be bonded to each other to form a ring.

  一种氟化方法，包括在微波和波长在微波区域附近的电磁波中的至少一种的辐照下，使基质和氟化剂相互反应，从而使基质氟化；其中基质选自由单羟基醇组成的组；具有多个羟基的多元醇；硫醇；具有羰基或羧基的化合物；由于存在引电子基团而亲核 性增强的芳香族化合物；芳香族重氮盐；寡糖和多糖；具有笼形的碳氢化合物；以及环氧 物；氟化剂由通式(I)表示： 其中 Y 代表氮原子或磷原子，R0、R1 和 R2 代表氢原子或可带有取代基的烷基或芳基，R0、R1 和 R2 所代表的原子和基团可以彼此相同或不同，R0、R1 和 R2 所代表的两个或三个基团可以彼此键合形成环。
• Method of fluorination by microwaves
  申请人：Mitsubishi Gas Chemical Company, Inc.

  公开号：EP2189467A2

  公开（公告）日：2010-05-26

  A method of fluorination which comprises fluorinating a substrate by bringing the substrate and a complex compound comprising HF and a base into reaction with each other under irradiation with at least one of microwave and electromagnetic wave having a wavelength around a microwave region; wherein the substrate is selected from the group consisting of a compound having hydrogen atom activated by a substituent at the α position, the β-position or the γ-position, a silyl ether compound, a compound having an unsaturated group, hydroxyl group, halogeno group, amino group, diazo group, triazeno group or isocyano group as a functional group, a saccharide and a cyclic compound having a three-membered or greater ring which may have a heteroatom.

  一种氟化方法，包括在微波和波长在微波区域附近的电磁波中的至少一种波长的辐照下，使基质和由氢氟酸和碱组成的复合物相互反应，从而使基质氟化； 其中基质选自由下列组成的化合物：在α位、β位或γ位有被取代基活化的氢原子的化合物；硅烷基醚化合物；具有不饱和基团、羟基、卤基、氨基、重氮基团、三氮基团或异氰基作为官能团的化合物；糖类和具有三元或三元以上环且可能具有杂原子的环状化合物。