Catalyst-Controlled Stereoselective O-Glycosylation: Pd(0) vs Pd(II) was written by Yao, Hui;Zhang, Shasha;Leng, Wei-Lin;Leow, Min-Li;Xiang, Shaohua;He, Jingxi;Liao, Hongze;Le Mai Hoang, Kim;Liu, Xue-Wei. And the article was included in ACS Catalysis in 2017.Quality Control of (6-Methoxypyridin-2-yl)methanol This article mentions the following:
Stereoselective construction of various O-glycosidic bonds was first achieved by different palladium sources using 3,4-O-carbonate galactal as the donor to reach yields up to 95% under mild conditions. With Pd(II) catalyst coordination of this glycal donor from the β-face directed by carbonate group, hard nucleophiles (aliphatic alcs.) gave β-glycosides and α-glycosides were obtained from soft nucleophiles (phenols). In contrast, with the Pd(0) catalyst coordinating the donor from the β-face due to steric effect, both hard and soft acceptors could only generate β-glycosides via hydrogen-bond-mediated aglycon delivery. In the experiment, the researchers used many compounds, for example, (6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5Quality Control of (6-Methoxypyridin-2-yl)methanol).
(6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Quality Control of (6-Methoxypyridin-2-yl)methanol
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem