70606-00-7

Usage

Uses

Used in Organic Synthesis:
(2R)-Tetrahydro-5-oxo-2β-furancarbaldehyde is used as a building block in organic synthesis for creating a variety of complex organic molecules. Its unique structure and functional groups allow for multiple reaction pathways, facilitating the synthesis of diverse chemical compounds.
Used in Pharmaceutical Industry:
(2R)-Tetrahydro-5-oxo-2β-furancarbaldehyde is used as an intermediate in the development of pharmaceuticals. Its reactivity and functional groups make it a valuable component in the synthesis of drug candidates, potentially leading to new treatments and therapies.
Used in Agrochemicals:
(2R)-Tetrahydro-5-oxo-2β-furancarbaldehyde is used as a reagent in the production of agrochemicals. Its chemical properties and reactivity contribute to the development of effective pesticides, herbicides, and other agricultural products.
Used in Chemical Research:
(2R)-Tetrahydro-5-oxo-2β-furancarbaldehyde is used as a subject of study in chemical research. Its unique structure and properties make it an interesting compound for scientists and researchers working in the field of organic chemistry and chemical synthesis, potentially leading to new discoveries and advancements in the field.

InChI:InChI=1/C5H6O3/c6-3-4-1-2-5(7)8-4/h3-4H,1-2H2

Upstream product

• 53558-94-4 (R)-(-)-γ-chlorocarbonyl-γ-butyrolactone 
• 52813-63-5 (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone 
• 59263-24-0 (R)-5-((1R,2R)-1,2,3-trihydroxypropyl)dihydrofuran-2(3H)-one 
• 137625-42-4 (-)-(4'R,5R)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydro-2(3H)-furanone 
• 69863-70-3 (R)-5-((S)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)dihydrofuran-2(3H)-one 
• 127940-36-7 (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 53558-93-3 (R)-tetrahydro-5-oxo-2-furancarboxylic acid 
• 6893-26-1 D-Glutamic acid 
• 56-86-0 L-glutamic acid 
• 126550-68-3 (R)-1-(benzyloxy)hex-5-en-2-ol 
• 77697-15-5 (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone 
• 312264-25-8 (5R)-2-(Z)-tert-butoxycarbonylmethylidene-5-[(1S)-1-acetyloxy-2-benzyloxyethyl]tetrahydrofuran 
• 184873-67-4 (R)-5-((S)-2-Benzyloxy-1-hydroxy-ethyl)-dihydro-furan-2-one 

Downstream Products

• 89103-56-0 3,5-trans-marmelo oxide 
• 74183-60-1 (2R,4R,5E)-2,7-Dimethyl-5,7-octadien-4-olide 
• 89103-56-0 3,5-cis-marmelo oxide 
• 89103-56-0 marmelo oxide A 
• 64726-91-6 japonilure 

Relevant academic research and scientific papers

Unexpected stereochemistry in the lithium salt catalyzed ring expansion of nonracemic oxaspiropentanes. Formal syntheses of (-)-(4R,5R)-muricatacin and the pheromone (R)-japonilure

(Matrix presented) The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2, depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the acetogenin (-)-(4R, SR)-muricatacin and the pheromone (R)-japonilure.

First total synthesis of the marine natural products clavulolactones II and III

The first total synthesis of the marine prostanoids clavulolactones II and III is presented from an easily accessible chiral, non-racemic cyclopentenone intermediate. Key steps involve selective TBDMS deprotection, selective reduction of the β-side chain and aldol condensation. Clavulolactones II and III were successfully prepared from (S)-4-((tert-butyldimethylsilyl)oxy) cyclopent-2-en-1-one over nine steps, in overall yields of 21 and 7% respectively. This journal is

Preparation of novel synthons, uniquely functionalized tetrahydrofuran and tetrahydropyran derivatives

The dianion of the acetoacetic ester reacts with epibromohydrin derivatives to afford a mixture of (Z)-2-alkoxycarbonylmethylidenetetrahydrofuran derivative and (E)-2-alkoxycarbonylmethylidenetetrahydropyran derivative. The selective formation of the tetr

Expeditious syntheses of sugar-modified nucleosides and collections thereof exploiting furan-, pyrrole-, and thiophene-based siloxy dienes

A series of individual sugar-modified pyrimidine nucleosides including enantiomerically enriched 2',3'-dideoxynucleosides 14a-c (α and β anomers of L- and D-series), 2',3'-dideoxy-4'-thionucleosides 21a-c (α and β anomers of L- and D-series), and 2',3'-dideoxy-4'-azanucleosides 28a-c (β anomers of L- and D-series) were synthesized, with uniform chemistry and high stereochemical efficiency, exploiting a triad of versatile heterocyclic siloxy dienes, namely, 2-(tert-butyldimethylsiloxy)furan (TBSOF), 2-(tert- butyldimethylsiloxy)thiophene (TBSOT), and N-(tert-butoxycarbonyl)-2-(tert- butyldimethylsiloxy)pyrrole (TBSOP). The synthetic procedure advantageously used both enantiomers of glyceraldehyde acetonide (D-1 and L-1) as sources of chirality and as synthetic equivalents of the formyl cation. The outlined chemistry also allowed for the rapid assemblage of a 30-member collection of racemic nucleosides (D,L-L) as well as one 15-member ensemble of chiral analogues (L-L), along with some related sublibraries.

MICROBIAL TRANSFORMATION OF (-)-VERNOLIC ACID INTO (4R,5R)-5-HYDROXY-γ-DECALACTONE

(-)-Vernolic acid, isolated and purified from seeds of Euphorbia lagascae was administered to cultures of Sporobolomyces odorus. (4R,5R)-5-Hydroxy-γ-decalactone 1 accumulated as the main product.The configuration of the product was determined by synthesis of all four stereoisomers and comparison of spectroscopic and chromatographic data.

A Convenient Synthesis of (R)-Japonilure

The title pheromone has been synthesised in high optical purity using easily accessible (S)-glycerol-2,3-acetonide (2) as the starting chiron.