Stereoselective intramolecular haloamidation of N-protected 3-hydroxy-4-pentenylamines and 4-hydroxy-5-hexenylamines was written by Tamaru, Yoshinao;Kawamura, Shinichi;Bando, Takashi;Tanaka, Kunitada;Hojo, Makoto;Yoshida, Zenichi. And the article was included in Journal of Organic Chemistry in 1988.Recommanded Product: 13417-49-7 This article mentions the following:
Haloamidation of N-(p-tolylsulfonyl)-3-hydroxy-4-pentenylamines proceeds regio- and stereoselectively to provide cis-2-(halomethyl)-3-hydroxypyrrolidines in high yields. The tosylamides with Ph and di-Me substituents at C-5 cyclize to give six-membered piperidine products. N-(Methoxycarbonyl)-3-hydroxy-4-pentenylamines undergo a similar cyclization to furnish cis-N-(methoxycarbonyl)-2-(halomethyl)-3-hydroxypyrrolidines, which further undergo a cyclization to give bicyclic oxazolidones (1-aza-3-oxabicyclo[3.3.0]octan-2-ones). The above reactions proceed in the dark, while the haloamidation of N-(p-tolylsulfonyl)-4-hydroxy-5-hexenylamine only proceeds upon exposure to ambient light and provides 2-(halomethyl)-3-hydroxypiperidine. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Recommanded Product: 13417-49-7).
5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. Pyran derivatives such as pyran flavonoids are biologically important. Monosaccharides containing six-membered rings are called pyranose.Recommanded Product: 13417-49-7
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics