Visible-light-promoted stereoselective C(sp3)-H glycosylation for the synthesis of C-glycoamino acids and C-glycopeptides was written by Qi, Rupeng;Wang, Chao;Ma, Zijian;Wang, Hongying;Chen, Qiao;Liu, Liangyu;Pan, Da;Ren, Xiaoyu;Wang, Rui;Xu, Zhaoqing. And the article was included in Angewandte Chemie, International Edition in 2022.Product Details of 367-93-1 The following contents are mentioned in the article:
The glycosylative modification of peptides could improve the pharmacol. properties of peptide drugs and deliver them efficiently to the target sites. Compared with O-/N-glycosides, C-glycosides exhibit more metabolic stability. We here disclose the first example of visible-light-promoted and Cu-catalyzed stereoselective C-glycosylation. The mild reaction conditions are compatible with various carbohydrate substrates, as demonstrated with a series of monosaccharides and a disaccharide, and are amenable to the synthesis of a wide variety of C-glycoamino acids and C-glycopeptidomimetics with good yields and excellent stereoselectivities. The dual-functional photocatalyst formed in situ via coordination of the glycine derivative and the chiral phosphine Cu complex could not only catalyze the photoredox process but also control the stereoselectivity of the glycosylation reaction. This study involved multiple reactions and reactants, such as (2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triol (cas: 367-93-1Product Details of 367-93-1).
(2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triol (cas: 367-93-1) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Product Details of 367-93-1
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts