Selective synthesis of 3-deoxy-5-hydroxy-1-amino-carbasugars as potential α-glucosidase inhibitors was written by Jiang, Chunfeng;Liu, Quan;Liu, Jiaming;Liu, Kaixuan;Tian, Liangliang;Duan, Mingfei;Wang, Ying;Shen, Zhufang;Xu, Youjun. And the article was included in Organic & Biomolecular Chemistry in 2019.Synthetic Route of C4H11NO This article mentions the following:
A convenient synthesis of novel 3-deoxy-5-hydroxy-1-aminocarbasugars was developed here. The benzyl-protected glucose-derived ketone was selectively converted in high yield to enone I via retro-Michael elimination of BnOH. The double bond of I was regio- and stereo-selectively reduced by the induction of C4-α-OBn to the multi-functionalized II . II contained all the functionalities with similar configurations to carbasugars but with 3-H and 5-OH in the ring, and it would be a very interesting building block for organic synthesis or for bioactive compounds As one application, II was further transformed into 1-amino-carbasugars, e.g. III, by the reductive amination and final deprotection of benzyl groups. The targets were subjected to the in vitro inhibitory activity test against sucrase or maltase. The inhibitory activity of III against sucrase was nearly similar to that of voglibose. In comparison with voglibose, in vivo results similarly showed that III could lower the post-prandial blood glucose level after sucrose loading in healthy male ICR mice, while miglitol or acarbose was less effective. The mol. modeling study of some targets or voglibose with human sucrase could explain the inhibiting action. In the experiment, the researchers used many compounds, for example, (R)-2-Aminobutan-1-ol (cas: 5856-63-3Synthetic Route of C4H11NO).
(R)-2-Aminobutan-1-ol (cas: 5856-63-3) 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. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Synthetic Route of C4H11NO
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts