121237-62-5Relevant academic research and scientific papers
IBr-catalyzed O-glycosylation of D-glucals: Facile synthesis of 2,3-unsaturated-o-glycosides
Saeeng, Rungnapha,Siripru, Onanong,Sirion, Uthaiwan
, p. 849 - 861 (2015)
Iodine monobromide (IBr) is explored as an alternative catalyst for the selective synthesis of 2,3-unsaturated glycosides from tri-O-acetyl-D-glucal 1 with several alcohols through Ferrier rearrangement. This reaction was shown to be a simple, efficient and cost-effective method, affords twenty examples of corresponding glycoside products in high yields with good α-selectivity.
Microwave-induced, InCl3-catalyzed Ferrier rearrangement of acetylglycals: Synthesis of 2,3-unsaturated glycopyranosides
Das, Saibal Kumar,Reddy, K. Anantha,Roy, Joyita
, p. 1607 - 1610 (2003)
Indium(III) chloride catalyzed, microwave assisted Ferrier rearrangement on different per-O-acetylglycals leads to an efficient synthesis of 2,3-unsaturated O-glycosides in good to excellent yields.
Radical Cyclisation of Some Unsaturated Carbohydrate Derived Acetals
Chapleur, Yves,Moufild, Nadira
, p. 39 - 40 (1989)
Haloacetals derived from pyranisidic allylic alcohols or allylic hemiacetals were stereospecifically cyclized using tributiltin hydride as radical promotor to give fused furanoses; the reaction was also applied to a propargylic glycoside which cyclized re
Catalytic tin radical mediated tricyclisations. Part 1. Monocyclisation studies
Kelly, David R.,Picton, Mark R.
, p. 1559 - 1569 (2000)
A general strategy for catalytic tin radical mediated, radical cascade reactions is proposed in which three rings are constructed in a single step. The initial step in the tricyclisation process has been examined using 2,3-dideoxy-α-D-erythro-hex-2-enopyr
Phosphomolybdic acid supported on silica gel: a mild, efficient and reusable catalyst for the synthesis of 2,3-unsaturated glycopyranosides by Ferrier rearrangement
Yadav,Satyanarayana,Balanarsaiah,Raghavendra
, p. 6095 - 6098 (2006)
A simple, mild, efficient and environmentally benign method for the synthesis of 2,3-unsaturated allyl C-glycosides and O- and S-glycosides is described using phosphomolybdic acid supported on silica gel as a reusable catalyst with high α-selectivity.
Bi(OTf)3 and SiO2-Bi(OTf)3 as effective catalysts for the ferrier rearrangement
Lokesh Babu,Khare, Anakshi,Vankar, Yashwant D.
, p. 884 - 892 (2005)
Bi(OTf)3 and SiO2-Bi(OTf)3 are found to effectively catalyze the Ferrier rearrangement of tri-O-acetyl glycals with different alcohols providing an effective route to 2,3-imsaturated O-glycosides with good anomeric selectivity and good to excellent yields after short reaction times.
A facile H2SO4/4 ? molecular sieves catalyzed synthesis of 2,3-unsaturated O -glycosides via ferrier-type rearrangement
Zhou, Jiafen,Zhang, Bo,Yang, Guofang,Chen, Xuan,Wang, Qingbing,Wang, Zhongfu,Zhang, Jianbo,Tang, Jie
, p. 893 - 896 (2010)
A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a metal-free catalytic system. This catalyst, sulfuric acid/4 molecular sieves can catalyze the reaction of 3,4,6-tri-O-acetyl-d-glucals and a wide range of alcohols at room temperature, affording 2,3-unsaturated glycosides in good -selectivity (α/β> 6:1) via a Ferrier-type rearrangement. Georg Thieme Verlag Stuttgart - New York.
Application of click chemistry towards an efficient synthesis of 1,2,3-1H-triazolyl glycohybrids as enzyme inhibitors
Anand, Namarata,Jaiswal, Natasha,Pandey, Sarvesh Kumar,Srivastava,Tripathi, Rama P.
, p. 16 - 25 (2011)
An efficient synthesis of novel 1,2,3-1H-triazolyl glycohybrids with two or more than two sugar units or a chromenone moiety via copper-catalysed azide-alkyne cycloaddition (CuAAC), a 1,3-dipolar cycloaddition of glycosyl azides to 2,3-unsaturated alkynyl glycosides or propargyloxy coumarins is described. The synthesised glycohybrids were screened for their α-glucosidase, glycogen phosphorylase and glucose-6-phosphatase inhibitory activities. A few of the glycohybrids showed promising inhibitory activities against these enzymes.
A Highly Efficient Magnetic Iron(III) Nanocatalyst for Ferrier Rearrangements
Chen, Heshan,Ding, Zekun,Dong, Youxian,Guo, Hong,Jiang, Nan,Qiu, Saifeng,Xu, Xiaoxia,Zhang, Jianbo,Zhou, Le
, p. 1419 - 1426 (2019/07/15)
A novel and highly efficient magnetic Fe 3 O 4 &at;C&at;Fe(III) core-shell catalyst, in which the carbon shell was prepared from lotus leaf, was fabricated. This nanocatalyst was successfully applied in the synthesis of a series of 2,3-unsaturated O- glycosides in excellent yields and with high selectivity, especially in the case of 2-halo O- glycosides, which differ in reactivity from nonsubstituted O- glycosides, but which have scarcely been explored before. Moreover, the catalyst could be easily separated from the reaction by the application of an external magnetic force and reused a minimum of five times without any significant decrease in the yields of the products. In addition, the reaction proceeded readily on a gram scale, which provides a bright prospect for future applications.
Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- And S-linked glycosides
Tatina, Madhu Babu,Mengxin, Xia,Peilin, Rao,Judeh, Zaher M. A.
supporting information, p. 1275 - 1280 (2019/07/08)
A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.
