benzyl N-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)carbamate | 764674-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)carbamate
• 英文别名: 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosylbenzyl carbamate
• CAS: 764674-85-3
• 化学式: C₁₈H₂₁NO₇
• 分子量: 363.367
• InChiKey: JMUPBEJXQCAGFU-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  氨基甲酸苄酯 、 乙酰化葡萄烯糖 在 hafnium tetrakis(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以76%的产率得到benzyl N-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)carbamate
  参考文献：
  名称：

  fin（IV）通过I型重排重排促进了2,3-不饱和N-和C-假糖苷的合成

  摘要：

  通过使用HF（OTF）4作为催化剂，一系列2,3- ñ -和ç不饱和葡糖苷已经从3,4,6-三-合成ö乙酰基d -glucal，2,4-， 6-三ö苄基d -glucal和（（2 - [R，3小号）-3-乙酰氧基-2,3-二氢呋喃-2-基）甲基乙酸酯以良好的收率与高选择性异头温和的反应条件下。

  DOI：

  10.1016/j.tetlet.2016.12.023

文献信息

• Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and<i>O</i>-Glycosylation of 1-<i>O</i>-Acetyl Sugars as Glycosyl Donors
  作者：Rashmi Roy、Parasuraman Rajasekaran、Asadulla Mallick、Yashwant D. Vankar

  DOI：10.1002/ejoc.201402606

  日期：2014.9

  have developed a new catalyst system comprising AuCl3 and phenylacetylene that promotes the Ferrier rearrangement of glycals and 2-acetoxymethylglycals with different nucleophiles, and also the O-glycosylation of 1-O-acetyl sugars to obtain a variety of useful glycosides at room temperature through relay catalysis. Good anomeric selectivity was observed for the Ferrier rearrangements, whereas the O-glycosylation

  我们开发了一种新的催化剂体系，包含 AuCl3 和苯乙炔，可促进具有不同亲核试剂的糖类和 2-乙酰氧基甲基糖类的费里尔重排，以及 1-O-乙酰糖的 O-糖基化，以通过以下方式在室温下获得各种有用的糖苷中继催化。对于 Ferrier 重排观察到良好的异头异构体选择性，而 1-O-乙酰糖的 O-糖基化产生具有中等至极好选择性的非对映异构体混合物。
• Gd(OTf) 3 catalyzed preparation of 2,3-unsaturated O -, S -, N -, and C -pyranosides from glycals by Ferrier Rearrangement
  作者：Peiran Chen、Jie Su

  DOI：10.1016/j.tet.2015.11.002

  日期：2016.1

  By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.

  通过使用Gd（OTf）3作为催化剂，已经通过Ferrier重排进行了2，3-不饱和糖苷的合成。一系列的2,3-不饱和ø - ，小号- ，Ñ - ，和Ç从3,4,6-三获得-glycosides ö乙酰基d -glucal，3,4,6-三- ø -苄基- d -glucal，和3,4-二- ö乙酰基升以良好的收率和高的选择性异头温和反应条件下-rhamnal。
• Aza-Ferrier rearrangement of glycals with amides promoted by molecular iodine
  作者：Zubeda Begum、Ch. Kishore、V. Veerabhadra Reddy、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2014.09.023

  日期：2014.10

  been achieved using an equimolar amount of molecular iodine under mild and neutral conditions to afford the corresponding N-glycosyl amides in good yields with a preferential α-anomeric selectivity. The use of iodine makes this method simple, convenient, and cost-effective. This is the first report on aza-Ferrier rearrangement using molecular iodine.

  的Amidoglycosidation三ö乙酰基d -glucal具有不同的N-亲核试剂如吨丁基氨基甲酸酯，Ñ -苄基氨基甲酸酯，Ñ -乙基氨基甲酸酯，甲苯磺酰基酰胺，和甲磺酰酰胺已根据使用分子碘等摩尔量达到在温和的中性条件下以良好的收率得到具有优先的α-异头异构体选择性的相应的N-糖基酰胺。碘的使用使该方法简单，方便且具有成本效益。这是有关使用分子碘进行氮杂-费雷尔重排的第一份报告。
• A mild and efficient synthetic protocol for Ferrier azaglycosylation promoted by ZnCl2/Al2O3
  作者：Feiqing Ding、Ronny William、Bala Kishan Gorityala、Jimei Ma、Siming Wang、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2010.04.045

  日期：2010.6

  An improved method for the Ferrier sulfonamidoglycosylation of tri-O-acetyl-D-glucal with different N-nucleophiles has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 3,4,6-tri-O-acetyl-D-glucal into 2,3-unsaturated-N-pseudoglycals with good yields and preferential alpha-anomeric selectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• An eco-friendly tandem tosylation/Ferrier N -glycosylation of amines catalyzed by Er(OTf) 3 in 2-MeTHF
  作者：Monica Nardi、Natividad Herrera Cano、Antonio De Nino、Maria Luisa Di Gioia、Loredana Maiuolo、Manuela Oliverio、Ana Santiago、Diletta Sorrentino、Antonio Procopio

  DOI：10.1016/j.tetlet.2017.03.047

  日期：2017.5

  Er(OTf)(3) in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N-nucleophiles. The stereoselective synthesis of 2,3-unsaturated-N-pseudoglycals was carried out with 3,4,6-tri-O-acetyl-d-glucal and different nucleophiles affording good results in a short time. (C) 2017 Published by Elsevier Ltd.