Ethyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-arabinohexopyranoside | 63069-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-arabinohexopyranoside
• 英文别名: ethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside；ethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose；[(2R,3S,4R,6S)-3,4-diacetyloxy-6-ethoxyoxan-2-yl]methyl acetate
• CAS: 63069-75-0
• 化学式: C₁₄H₂₂O₈
• 分子量: 318.324
• InChiKey: FYRWMXQGVDQCTF-MQYQWHSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-arabinohexopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 Acetic acid (2R,3S,4R,6S)-4-acetoxy-6-ethoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A mild and simple enzymic conversion of aldono- and aldurononitriles into the corresponding amides and/or carboxylic acids

  摘要：

  DOI：

  10.1021/jo00063a048
• 作为产物：
  描述：

  2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.5h， 生成 Ethyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-arabinohexopyranoside
  参考文献：
  名称：

  2-脱氧-α-和β-D-Glucopyranosyl4'-Bromoisoquinolinium四氟硼酸盐的溶剂化物。

  摘要：

  在含水甲醇，乙醇，三氟乙醇以及乙醇和三氟乙醇的二元混合物中监测2-脱氧-α-和β-D-吡喃葡萄糖基4'-溴代异喹啉鎓四氟硼酸盐的溶剂化物（1和2）。观察到的速率常数与通过解离（D（N）A（N））过渡态进行的1和2的溶剂解一致。与α-异头物相比，β-化合物的溶剂分解使过渡态电荷离域到环氧原子上更大。溶剂分解产物比率的分析表明，在所研究的溶剂混合物中，2-脱氧葡萄糖基氧杂碳鎓离子未达到溶剂平衡。在化合物1的溶剂分解中，溶剂三氟乙醇有助于离去基团的扩散分离，因此，

  DOI：

  10.1021/jo0004106

文献信息

• Synthetic utility of 1,1,2,2-tetraaryldisilanes: radical reduction of alkyl phenyl chalcogenides
  作者：Osamu Yamazaki、Hideo Togo、Masataka Yokoyama

  DOI：10.1039/a905937g

  日期：——

  Reactivity of tetraaryldisilanes as radical reducing agents of alkyl phenyl chalcogenides initiated by Et3B or AIBN was studied. Here, the reactivity of alkyl sulfide was poor; however, various alkyl phenyl selenides and tellurides were reduced to the corresponding hydrocarbons in good yields with 1,1,2,2-tetraphenyldisilane.

  研究了由Et 3 B或AIBN引发的四芳基乙硅烷作为烷基苯基硫族化物自由基还原剂的反应性。在此，烷基硫化物的反应性差。但是，用1,1,2,2-四苯基乙硅烷可将各种烷基苯基硒化物和碲化物以良好的收率还原为相应的烃类。
• AuCl₃-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives
  作者：Robin Jeanneret、Carlo Walz、Maarten van Meerbeek、Sarah Coppock、M. Carmen Galan

  DOI：10.1021/acs.orglett.2c02530

  日期：2022.9.2

  A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α′-linked 2-deoxy trehalose analogues via AuCl3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.

  描述了一种使用半缩醛糖基供体和受体通过 AuCl 3催化的脱水糖基化直接获得 1,1-α,α'-连接的 2-脱氧海藻糖类似物的实用、催化和高度立体选择性的新方法。该方法依赖于在其他反应性较低的半缩醛存在下，三苯甲基化 2-脱氧半缩醛的化学选择性布朗斯台德酸型活化。
• Erosion of Stereochemical Control with Increasing Nucleophilicity: <i>O</i>-Glycosylation at the Diffusion Limit
  作者：Matthew G. Beaver、K. A. Woerpel

  DOI：10.1021/jo902222a

  日期：2010.2.19

  Nucleophilic substitution reactions of 2-deoxyglycosyl donors indicated that the reactivity of the oxygen nucleophile has a significant impact on stereoselectivity. Employing ethanol as the nucleophile resulted in a 1:1 (alpha:beta) ratio of diastereomers under S(N)1-like reaction conditions. Stercoselective formation of the 2-deoxy-alpha-O-glycoside was only observed when weaker nucleophiles, such as trifluoroethanol, were employed. The lack of stercoselectivity observed in reactions of common oxygen nucleophiles can be attributed to reaction rates of the stereochemistry-determining step that approach the diffusion limit. In this scenario, both faces of the prochiral oxocarbenium ion are subject to nucleophilic addition to afford a statistical mixture of diastercomeric products. Control experiments confirmed that all nucleophilic substitution reactions were performed under kinetic control.
• Direct preparation of 2-deoxy-D-glucopyranosides from glucals without Ferrier rearrangement
  作者：Veronique Bolitt、Charles Mioskowski、S. G. Lee、J. R. Falck

  DOI：10.1021/jo00310a006

  日期：1990.11
• Synthesis of 2-deoxy-L- and -D-galacto-heptose via inverse type hetero-diels-alder reaction
  作者：Luigi De Gaudenzi、Satyam Apparao、Richard R. Schmidt

  DOI：10.1016/s0040-4020(01)97598-2

  日期：1990.1