3539-39-7

Usage

Chemical class

1-propanols

Ether functional group

tetrahydro-2H-pyran-2-yl

Common uses

solvent, intermediate for synthesis of various compounds

Known for

ability to dissolve a wide range of substances

Utilized in

production of pharmaceuticals, flavorings, fragrances, cosmetics, dyes, and printing inks

Toxicity

moderate, should be handled with care to avoid harmful effects on human health and the environment.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 3539-40-0 Ethyl (S)-(-)-2-tetrahydropyran-2-yloxypropionate 

Downstream Products

• 124410-01-1 (S)-(-)-3,4-difluoro-2-[2-(2-tetrahydropyranyloxy)propoxy]nitrobenzene 
• 143331-41-3 (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane 
• 42274-61-3 (S)-(-)-2-(tetrahydropyranyloxy)propyl p-toluenesulfonate 
• 129798-50-1 (R)-3-chloro-4-fluoro-2-[2-(2-tetrahydropyranyloxy)propoxy]nitrobenzene 

Relevant academic research and scientific papers

New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-, Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands

Eleven new chiral macrocycles (1-11, see Figure 1) of the pyridino-18-crown-6 type have been prepared.Nine diazapyridino-crown ligands contain two amide (1, R = benzyl; 4, R = phenyl), two N-methylamide (7, R = phenyl), two thionoamide (2, R = benzyl; 5,

An (S)-(+)-Lactic Acid Route to (2S,6R,8S)-2,8-Dimethyl-1,7-dioxaspiroundecane and (2S,6R,8S)-2-Ethyl-8-methyl-1,7-dioxaspiroundecane and Demonstration of their Presence in the Rectal Glandular Secretion of Bactrocera nigrotibialis (Perkin)

The chiral iodide resulting from reduction and iodination of the tetrahydropyran-2-yl ether of ethyl (S)-(+)-lactate has been engaged in a free-radical addition to acrylonitrile.The resulting protected hydroxy nitrile, on reaction with pent-4-enylmagnesium bromide afforded (S)-2-tetrahydropyran-2-yloxyundec-10-en-6-one.Oxymercuration of this hydroxy enone, under reversible conditions, employing aqueous acid-tetrahydrofuran, effected simultaneous deprotection and cyclisation, and in situ biphasic demercuration with sodium borohydride provided essentially stereochemically pure (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiroundecane .Epoxidation of the protected hydroxy enone, followed by dimethylcuprate ring-opening and cyclisation, provided a mixture of the (E,E) and the two possible (E,Z)-diastereomers of 2-ethyl-8-methyl-1,7-dioxaspiroundecane with the former being the (2S,6R,8S) stereoisomer.Separation of the (E,E) from the two (E,Z) isomers was achieved by preparative gas chromatography.GC analysis of these samples and of the rectal glandular secretion of male Bactrocera nigrobialis, using a cyclodextrin-based phase, demonstrated that (2S,6R,8S)-stereoisomers of the 2,8-dimethyl-and 2-ethyl-8-methyl-1,7-dioxaspiroundecanes were the natural products, with no detectable level of the antipodes.