7310-51-2

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 7017, 1991 DOI: 10.1016/0040-4039(91)85028-4

Upstream product

• 694-54-2 tetrahydro-2H-2-pyranol 
• 106-95-6 allyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 4221-03-8 5-hydroxypentanal 
• 69161-61-1 2-(prop-2-en-1-yloxy)oxane 
• 693-03-8 n-butyl magnesium bromide 
• 110-87-2 3,4-dihydro-2H-pyran 
• 87086-60-0 tetrahydro-6-(2-propenyl)pyran-2(2H)-one 
• 60222-90-4 5-hydroxy pentanaloxime 
• 107-18-6 allyl alcohol 

Downstream Products

• 1231182-93-6 C₁₅H₂₀O₃ 

Relevant academic research and scientific papers

Indium trichloride-catalyzed indium-mediated allylation of dihydropyrans and dihydrofurans in water

A one-pot indium trichloride-catalyzed indium-mediated allylation of dihydropyrans and dihyfrofurans has been found to be feasible. This catalytic system afforded the allylated diols in moderate to high yields.

A general electron transfer reduction of lactones using SmI 2-H2O

Herein we describe a strategy for the selective, electron transfer reduction of lactones of all ring sizes and topologies using SmI 2-H2O and a Lewis base to tune the redox properties of the complex. The current protocol permits instantaneous reduction of lactones to the corresponding diols in excellent yields, under mild reaction conditions and with useful chemoselectivity. We demonstrate the broad utility of this transformation through the reduction of complex lactones and sensitive drug-like molecules. Sequential electron transfer reactions and syntheses of deuterated diols are also described.

FeCl3-catalysed Zn-mediated allylation of cyclic enol ethers in water

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One-pot sequential deoximation and allylation reactions of aldoximes in aqueous solution

A simple procedure has been developed for conducting tin-mediated deoximation and allylation reactions of aldoximes in water to form homoallylic alcohols. Employing the new conditions, various homoallylic alcohols were produced in good to excellent yields

Tin mediated allylation reactions of enol ethers in water

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Evaluation of the key aroma compounds in beef and pork vegetable gravies a la chef by stable isotope dilution assays and aroma recombination experiments

Although the aroma compounds of meat processed as such have been studied previously, data on complete homemade dishes containing beef and pork meat were scarcely studied. Recently, 38 odor-active compounds were characterized in beef and pork vegetable gravies using GC-olfactometry. In the present investigation, the most odor-active compounds were quantitated in a freshly prepared stewed beef vegetable gravy (BVG) as well as a stewed pork vegetable gravy (PVG) by means of stable isotope dilution assays. Calculation of odor activity values (OAVs; ratio of concentration to odor threshold) revealed 3-mercapto-2- methylpentan-1-ol, (E,E)-2,4-decadienal, (E,Z)-2,6-nonadienal, (E)-2-decenal, (E)-2-undecanal, and 3-hydroxy-4,5-dimethyl-2(5H)-furanone as the most potent odorants in both gravies. However, significantly different OAVs were found for 12-methyltridecanal, which was much higher in the BVG, whereas (E,Z)-2,4-decadienal showed a clearly higher OAV in the PVG. Aroma recombination experiments performed on the basis of the actual concentrations of the odorants in both gravies revealed a good similarity of the aromas of both model mixtures containing all odorants with OAVs > 1 with those of the original gravies.

Design and synthesis of novel fluoro amino acids: synthons for potent macrocyclic HCV NS3 protease inhibitors

The Hepatitis C Virus (HCV) is a major health hazard and its infection is a leading cause of chronic liver disease world wide. In our efforts toward the discovery of a back up to our first clinical candidate, Boceprevir (SCH 503034), we approached the depeptidization of the molecule through macrocyclization. Herein we report the design and synthesis of fluoro amino acids with desired stereochemistry required for the synthesis of macrocyclic inhibitors with fluorine at various positions of the aliphatic chain. Biological activities of representative examples are also reported.

Use of allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3-, C4-, and C5-carbon sources: Palladium-catalyzed allylation of aldehydes

Palladium-diethylzinc or palladium-triethylborane catalytically promotes self-allylation of 2-(allyloxy)tetrahydrofurans, 2-(allyloxy)tetrahydropyrans, and their hydroxy derivatives on the rings (ribose, glucose, mannose, deoxyribose, deoxyglucose). All the reactions proceed at room temperature and provide polyhydroxyl products, sharing a structural motif of a homoallyl alcohol, in good to excellent yields with high levels of stereoselectivity. Useful Crunit elongation, which makes the best use of an allyl ether as a protecting group and a nucleophilic allylation agent, is demonstrated. Mechanisms for the umpolung reaction (of an allyl ether into an allylic anion) and stereoselectivity associated with allylation of aldehydes are discussed.

Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols

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Formation of manganese-alkyne complexes mediated by trialkylmanganates and their application

Treatment of dodec-6-yne with triallylmanganate in the presence of 1,3,5-trimethylbenzene provides (Z)-dodec-6-ene. An addition of D2O before quenching the reaction affords the corresponding dideuterated alkene. The result suggests the existence of the manganese-alkyne complex as an intermediate. Treatment of methyl propargyl ethers as alkynes with tributylmanganate generates propargylmanganese species. The reaction of non-2-ynyl tetrahydropyran-2-yl ether with tributylmanganate provides tetradec-7-yn-1,5-diol and 6-hexylocta-6,7-dien-1,5-diol.