208523-33-5Relevant academic research and scientific papers
Zinc p-tert-butylbenzoate catalyzed glycosylation with glycopyranosyl chloride
Nishizawa,Garcia,Shin,Yamada
, p. 784 - 785 (1993)
A 0.1 eq of zinc p-tert-butylbenzoate significantly accelerates glycosylation of alcohol with glycopyranosyl chloride in the presence of 2-methyl-2-butene to give β-glycoside in high yield with fair to good β-selectivity.
A selective electrochemical method of glycosylation of 3β-hydroxy-Δ5-steroids
Morzycki, Jacek W.,?otowski, Zenon,Siergiejczyk, Leszek,Wa?ejko, Piotr,Witkowski, Stanis?aw,Kowalski, Jan,P?oszyn?ska, Jolanta,Sobkowiak, Andrzej
, p. 1051 - 1055 (2010)
A new electrochemical glycosylation method is presented. According to the method cholesterol and other 3β-hydroxy-Δ5-steroids can be selectively transformed to glycosides using non-activated sugars. The method is also useful for the synthesis of glycoconjugates with sugar linked to a steroid moiety by an ether bond.
Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group
Shaw, Mukta,Thakur, Rima,Kumar, Amit
, p. 589 - 605 (2019/01/14)
An efficient and operationally simple gold(III)-catalyzed glycosylation protocol was developed using newly synthesized benchtop stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate a
Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate
Tomkiel, Aneta M.,Siergiejczyk, Leszek,Naróg, Dorota,P?oszyńska, Jolanta,Sobkowiak, Andrzej,Morzycki, Jacek W.
, p. 44 - 51 (2016/12/26)
Electrochemical cholesterylation of various sugars with cholesteryl diphenylphosphate was studied. The reaction afforded mono-, di-, tri-, and tetra-cholesterylated products using equivalent amounts of the reagent. The reactions turned out to be completel
ortho-(Methyltosylaminoethynyl)benzyl glycosides as new glycosyl donors for latent-active glycosylation
Chen, Xiaoping,Shen, Dacheng,Wang, Qiaoling,Yang, You,Yu, Biao
, p. 13957 - 13960 (2015/09/07)
A new glycosylation protocol employing ortho-(methyltosylaminoethynyl)benzyl glycosides as glycosyl donors and TMSOTf as the catalyst is disclosed. These donors can be readily prepared from the corresponding 'latent' ortho-iodobenzyl glycosides via a Sonogashira coupling, thus providing a new approach for the 'latent-active' synthesis of glycans.
Ortho-Alkynylphenyl thioglycosides as a new type of glycosylation donors under the catalysis of Au(I) complexes
Yang, Fei,Wang, Qiaoling,Yu, Biao
, p. 5231 - 5234 (2012/11/13)
ortho-Alkynylphenyl thioglycosides, prepared readily via Sonagashira coupling of ortho-bromophenyl thioglycosides with alkynes, could undergo glycosidation effectively under the catalysis of a gold(I) complex.
An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf
Li, Yao,Yang, You,Yu, Biao
, p. 3604 - 3608 (2008/09/21)
A new and powerful glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors and Ph3PAuOTf as a promoter is disclosed. The donors are readily available and stable; the glycosidic coupling yields are generally excellent; the promotion system is catalytic, neutral, and orthogonal to the known glycosylation conditions.
Propargyl glycosides as stable glycosyl donors: Anomeric activation and glycoside syntheses
Hotha, Srinivas,Kashyap, Sudhir
, p. 9620 - 9621 (2007/10/03)
The advantages of stable glycosyl donors for saccharide coupling are many, and we describe herein the utility of propargyl glycosides for anomeric activation and glycoside synthesis exploiting the alkynophilicity of AuCl3. Various aglycones wer
Catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate
Matsuo, Jun-Ichi,Shirahata, Tatsuya,Omura, Satoshi
, p. 267 - 271 (2007/10/03)
Catalytic and stereoselective glycosylation efficiently proceeded by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acids in the presence of a glycosyl acceptor and molecular sieves 5 ?. Catalytic and one-pot dehydrative
Activation of glycosyl phosphites under neutral conditions in solutions of metal perchlorates in organic solvents
Schene, Heidrun,Waldmann, Herbert
, p. 1227 - 1230 (2007/10/03)
Glycosyl phosphites 1-3 derived from glucose are activated under neutral conditions and without the addition of any further promoter in 1 M solutions of LiClO4, Mg(ClO4)2 or Ba(ClO4)2 in ether, CHsub
