114817-97-9Relevant articles and documents
Direct Elaboration of Pent-4-enyl Glycosides Into Disaccharides
Fraser-Reid, Bert,Konradsson, Peter,Mootoo, David R.,Udodong, Uko
, p. 823 - 825 (1988)
Pent-4-enyl glycosides, on treatment with halonium ions, become chemospecifically activated so that coupling with partially protected monosaccharides can be effected, leading to the in situ formation of disaccharides.
Convenient use of ortho-formylphenyl thioglycoside for regioselective conjugation with glycosyl acceptors towards regioselective 1,2-cis-glycosylation
Dohi, Hirofumi,Komai, Ryota,Sakai, Hidetoshi,Komuro, Haruka,Nishida, Yoshihiro
, p. 307 - 324 (2017)
A facile methodology is proposed for regioselective conjugation between glycosyl donors and acceptors towards the development of regioselective 1,2-cis-glycosylation method. ortho-Formylphenyl 1-thio-β-d-galactopyranoside was regioselectively tethered to
Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis
Dohi, Hirofumi,Sakurai, Risa,Tamura, Manami,Komai, Ryota,Nishida, Yoshihiro
, p. 45 - 65 (2021/05/26)
Herein, o-(methoxycarbonyl)phenyl thioglycosides [or (methyl)salicyl 1-thioglycosides] were evaluated as non-malodorous thioglycoside alternatives. The o-methoxycarbonyl group was expected to assist in the departure of leaving group. Salicyl-type thioglyc
Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions
Chang, Chun-Wei,Lin, Mei-Huei,Chan, Chieh-Kai,Su, Kuan-Yu,Wu, Chia-Hui,Lo, Wei-Chih,Lam, Sarah,Cheng, Yu-Ting,Liao, Pin-Hsuan,Wong, Chi-Huey,Wang, Cheng-Chung
, p. 12413 - 12423 (2021/05/03)
The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.
Ferrocenium complex aided: O-glycosylation of glycosyl halides
Bauer, Eike B.,Talasila, Deva Saroja
, p. 36814 - 36820 (2021/12/02)
A new strategy for the activation of glycosyl halide donors to be utilized in glycosylation reactions is presented, utilizing the ferrocenium (Fc) complexes [FcB(OH)2]SbF6 and FcBF4 as promoters. The scope of the new system has been investigated using glycosyl chloride and glycosyl fluoride donors in combination with common glycosyl acceptors, such as protected glucose. The corresponding glycosylation products were formed in 95 to 10% isolated yields with α/β ratios ranging from 1/1 to β only (2 to 14 h reaction time at room temperature, 40 to 100% ferrocenium promoter load). This journal is
Catalytic and Atom-Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts
Hammelev, Christian H.,Pedersen, Christian M.,Yang, Liang
, (2020/05/16)
Benzylated glycosyl formates have been synthesized in one step from the corresponding hemiacetal or orthoester with formic acid as the sole reagent. The glycosyl formates are used as glycosyl donors under catalytic conditions with cheap metal catalysts ba
α-Selective glycosylations using glycosyl: N-(ortho-methoxyphenyl)trifluoroacetimidates
Kowalska, Karolina,Pedersen, Christian Marcus
supporting information, p. 1918 - 1925 (2020/03/23)
Six N-(o-methoxyphenyl)trifluoroacetimidate glycosyl donors have been synthesized and their role as glycosyl donors has been investigated. The donors were synthesized with complete -selectivity, except in one case, and were found to be stable. When Bi(OTf
A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide–Triflic Acid Catalysis
Geringer, Scott A.,Singh, Yashapal,Hoard, Daniel J.,Demchenko, Alexei V.
, p. 8053 - 8063 (2020/06/05)
Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl do
Indolylthio glycosides as effective building blocks for chemical glycosylation
Demchenko, Alexei V.,Shrestha, Ganesh,Panza, Matteo,Singh, Yashapal,Rath, Nigam P.
, p. 15885 - 15894 (2021/01/19)
The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.
Palladium-Catalyzed C-S Bond Formation as a Tool for Latent-Active Glycosylation
Hedberg, Christinne,Jessen, Kamilla S.,Hansson, Rikke F.,Heuckendorff, Mads,Jensen, Henrik H.
, p. 7068 - 7072 (2020/10/02)
A high-yielding palladium-catalyzed C-S cross-coupling is presented for utilization in carbohydrate chemistry as a key transformation for attachment of a second chelating sulfur atom that allows the exploitation of a latent-active glycosylation strategy w
