40595-23-1

Usage

Chemical Properties

Clear Oil

Uses

3-[(Tetrahydro-2H-pyran-2-yl)oxy]-1-butanol (cas# 40595-23-1) is a compound useful in organic synthesis.

Upstream product

• 104372-23-8 ethyl 3-(tetrahydropyranyloxypropyl)butanoate 
• 110-87-2 3,4-dihydro-2H-pyran 
• 77564-41-1 (R)-1,3-butanediol 1-benzyl ether 3-THP ether 
• 121652-34-4 3-(tetrahydro-pyran-2-yloxy)-butyric acid methyl ester 
• 79016-08-3 ethyl (R)-β-tetrahydropyranyloxybutyrate 
• 18826-95-4 1.3-butanediol 

Downstream Products

• 77564-43-3 (R)-3-<(tetrahydro-2H-pyranyl)oxy>butyl p-toluenesulfonate 

Relevant academic research and scientific papers

A facile total synthesis of neurotrophic metabolite (+/-)-neuchromenin

The synthesis of (+/-)-neuchromenin, a known natural product that induces neurite outgrowth of PC12 cells, is described. The total synthesis involved constructing a chromone ring from sesamol and coupling this intermediate to an aldehyde by a Morita-Baylis-Hillman reaction (MBH). The MBH adduct was cyclized under acidic conditions followed by removal of a methylene group to afford (+/-)-neuchromenin in 9 steps from sesamol.

12-Substituted-13,14-dihydroretinols designed for affinity labeling of retinol binding- and processing proteins

All-trans- and 11-cis-retinol derivatives substituted with various electron-withdrawing groups at C12 were designed to be affinity labels for retinol binding and processing proteins. Unlike other non-selective highly reactive affinity labels, these compounds carry a Michael acceptor type substitution at C12 of the polyene chain. Therefore, they are expected to be highly selective towards such proteins that have a nucleophilic residue near the C11 position of their retinol ligand. The synthetic route for these compounds is based on the Emmons-Horner reaction of a C15 aldehyde with an appropriate phosphonate bearing the desired electron-withdrawing group to be incorporated at the C12 position of the retinol skeleton. Graphical abstract

Asymmetric addition of an electrophile to naphthalenes promoted and stereodirected by alcohol

4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) reacts with 1-methoxy-4-methylnaphthalene to give the 1,4-addition product in the presence of methanol; the reaction does not proceed in the absence of the alcohol. Methoxy exchange (with CD3OD) was al

Synthesis of racemic 8-nonene-2,4-diol, acyclic precursor of 1,3-dimethyl-1,9-dioxabicyclo[3.1.1]nonane

A new way of synthesis was developed for racemic 8-nonene-2,4-diol, the acyclic precursor of 1,3-dimethyl-1,9-dioxabicyclo[3.1.1]nonane. The latter substance was isolated from the bark of an ordinary spruce affected with a pest Trypodendron Lineatum Oliv.

Substrate structure and incubation-parameter-dependent selectivities in chiral discrimination of galactopyranosides by β-galactosidase hydrolysis

Mono-β-galactopyranosides of (+/-)-propane-1,2-diol, (+/-)-butane-1,3-diol, (+/-)-pentane-1,4-diol, (+/-)-butan-2-ol, (+/-)-pentan-2-ol and (+/-)-1,2-O-isopropylideneglycerol were synthesized by the Koenigs-Knorr reaction using hydroxycarbonyl compounds as precursors for the diolic substrates.Hydrolysis of 3-hydroxybutyl β-D-galactopyranoside 18 by β-galactosidases from Eschrichia coli, Aspergillus oryzae, Kluyveromyces lactis and Bacillus circulans, respectively, resulted in each case in an enantiomeric enrichment of the released diol.This was most significant with the E. coli enzyme and and increased with higher reaction temperature and shorter incubation periods.Under standartized conditions, cleavage of all synthesized galactopyranosides by this enzyme showed the highest stereoselectivity for butane-1,3-diol, butan-2-ol and isopropylideneglycerol with enantiomeric excesses in the range 60-75percent.For compounds with structural similarity to the natural substrate lactose, enhanced stereodiscriminations were expected.However, this could not be confirmed and instead a specific hydrophobic interaction is suggested to play a crucial role.

SYNTHESIS OF THE PROPIONATES OF (2R,8R)- AND (2S,8R)-8-METHYL-2-DECANOL, THE PHEROMONE OF THE WESTERN CORN ROOTWORM, EMPLOYING CHIRAL COMPOUNDS OF MICROBIAL ORIGIN AS STARTING MATERIALS

The attractants of the western corn rootworm (Diabrotica virgifera virgifera Le Conte), the propionates of (2R,8R)- and (2S,8R)-8-methyl-2-decanol, were synthesized from (R)-(+)-citronellol and the enantiomers of ethyl β-hydroxybutyrate of microbial origin.

SYNTHESIS OF TREE STEREOISOMERIC FORMS OF 2,8- DIMETHYL-1,7-DIOXASPIROUNDECANE, THE MAIN COMPONENT OF THE CEPHALIC SECRETION OF ANDRENA WILKELLA

Three stereoisomers of 2,8-dimethyl-1,7-dioxaspiroundecane were synthesized from acetoacetic ester by utilizing its yeast reduction and dianion alkylation.