19488-48-3Relevant articles and documents
Cleavage pattern of alkoxy- or aryloxymethyl ethers induced by mixed hydrides
Bajza, Istvan,Varga, Zsolt,Liptak, Andras
, p. 1991 - 1994 (1993)
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A novel, reductive ring-opening of carbohydrate benzylidene acetals, with unusual regioselectivity
Garegg, Per J.,Hultberg, Hans
, p. C10 - C11 (1981)
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Methyl 4-O-β-D-galactopyranosyl α-D-glucopyranoside (methyl α-lactoside)
Pan, Qingfeng,Noll, Bruce C.,Serianni, Anthony S.
, p. o674-o677 (2005)
Methyl α-lactoside, C13H24O11, (I), is described by glycosidic torsion angles φ (O5gal-C1 gal-O1gal-C4glc) and Ψ (C1 gal-O1gal-C4glc-C5glc/
A Chiral Copper Catalyzed Site-Selective O-Alkylation of Carbohydrates
Ren, Bo,Wang, Jiaxi,Zhang, Mengyao,Chen, Yue,Zhao, Wei
supporting information, p. 665 - 670 (2021/12/02)
Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper c
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
supporting information, 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.