104010-72-2

Usage

Uses

Used in Pharmaceutical Industry:
(+)-(3AS,6AS)-3A,6A-DIHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-ONE is used as an intermediate in the synthesis of Queuine (Q525000) for its role in the genetic code and protein synthesis. The compound contributes to the development of new drugs and therapies that target the fundamental processes of life, such as protein synthesis and gene expression.
Used in Biochemical Research:
In the field of biochemical research, (+)-(3AS,6AS)-3A,6A-DIHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-ONE is utilized as a key compound in the study of tRNA structure and function. Understanding the role of Queuine in tRNAs can lead to insights into various biological processes and the development of novel therapeutic strategies.
Used in Diagnostic Applications:
(+)-(3AS,6AS)-3A,6A-DIHYDRO-2,2-DIMETHYL-4H-CYCLOPENTA-1,3-DIOXOL-4-ONE can be employed in the development of diagnostic tools and tests that focus on the analysis of tRNA modifications and their implications in various diseases and conditions. This can help in the early detection and monitoring of diseases related to genetic mutations and protein synthesis disorders.

InChI:InChI=1/C8H10O3/c1-8(2)10-6-4-3-5(9)7(6)11-8/h3-4,6-7H,1-2H3/t6-,7+/m0/s1

Upstream product

• 34939-91-8 dimethyl lithiomethylphosphonate 
• 196497-20-8 (1R,5S,8R)-8-methoxy-3,3-dimethyl-2,4,7-trioxabicyclo[3.3.0]octan-6-one 
• 120623-91-8 (3aS,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one 
• 113565-13-2 (3αS,4R,6S,6αR)-4β-acetoxy-2,2-dimethyl-6-hydroxy-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxole 
• 116893-13-1 C₂₆H₃₀O₆ 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 77-76-9 2,2-dimethoxy-propane 
• 111570-91-3 4,5-dehydro-5-deoxy-2,3-O-isopropylidene-D-erythro-pentafuranose 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 634905-46-7 (4R,5S)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-1-(hydroxymethyl)-2-propen-1-ol 
• 103056-56-0 (+/-)-cis-4-phenyloxy-2-cyclopenten-1-ol 
• 122774-86-1 6-bromo-3,5-epoxy-1,2,3a,4,5,6,7,7a-octahydro-1,2-isopropylidenedioxy-4,7-methano-1H-indene 
• 6991-65-7 (3aR,4R,6aS)-4-methoxy-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole 
• 524939-62-6 4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 

Downstream Products

• 114948-34-4 (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 
• 180524-82-7 (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol 
• 869476-97-1 (3aS,6aS)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 910138-75-9 (+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol 
• 869477-01-0 [(3aR,4E,5R,6aS)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester 
• 683276-45-1 4,5-dihydroxy-2-prop-(Z)-enyl-cyclopent-2-enone 
• 683276-45-1 4,5-dihydroxy-2-prop-(E)-enyl-cyclopent-2-enone 
• 683276-31-5 (3aS,6aS)-2,2-dimethyl-5-prop-(Z)-enyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 683276-30-4 (3aS,6aS)-2,2-dimethyl-5-prop-(E)-enyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 332913-38-9 Trifluoro-methanesulfonic acid (R)-4-(3-methoxy-phenyl)-4-methyl-5-oxo-cyclopent-1-enyl ester 
• 158531-23-8 (3aS,4S,6aS)-5-Bromo-2,2-dimethyl-4-phenyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 
• 1053697-31-6 (3aS,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester 
• 112318-10-2 9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl)-3-deazaadenine 

Relevant academic research and scientific papers

Synthesis of the transfer-RNA nucleoside queuosine by using a chiral allyl azide intermediate

Chilled out: Chiral allyl azides are rarely used in natural product synthesis because of their tendency to undergo a [3.3] sigmatropic rearrangement (see scheme, top). In allylic cyclopentenyl azides, this rearrangement can be suppressed at just 0°C, enabling a short convergent synthesis of the hypermodified transfer-RNA nucleoside queuosine. (Chemical Equation Presented).

Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development

Clopidogrel is a prodrug anticoagulant with active metabolites that irreversibly inhibit the platelet surface GPCR P2Y12 and thus inhibit platelet activation. However, gaining an understanding of patient response has been limited due to imprecise understanding of metabolite activity and stereochemistry, and a lack of acceptable analytes for quantifying in vivo metabolite formation. Methods for the production of all bioactive metabolites of clopidogrel, their stereochemical assignment, and the development of stable analytes via three conceptually orthogonal routes are disclosed. (Chemical Equation Presented).

Improved and alternative synthesis of D- and L-cyclopentenone derivatives, the versatile intermediates for the synthesis of carbocyclic nucleosides

Improved and alternative syntheses of D- and L-cyclopentenone derivatives were achieved in six steps from D-ribose via ring-closing metathesis (RCM) reaction as a key step. These derivatives serve as very versatile intermediates for the synthesis of carbocyclic nucleosides.

Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (smallpox, monkeypox and cowpox)

An improved method for the synthesis of enantiomerically pure D-cyclopentenyl nucleosides has been accomplished and their antiviral activity against orthopox viruses have been evaluated. The key intermediate, L-cyclopent-2-enone 13 was prepared from D-ribose using a ring closing metathesis reaction in eight steps. Among the synthesized nucleosides, the adenine 2 (Neplanocin A), cytosine 14, and 5-F-cytosine 15 analogues exhibited potent anti-orthopox virus activity, including smallpox virus.

A NEW ROUTE TO (+)-2,3-(ISOPRPOPYLIDENEDIOXY)-4-CYCLOPENTENONE VIA THE OPTICALLY ACTIVE DICYCLOPENTADIENE INTERMEDIATE

Chiral synthesis of the dicyclopentadiene derivative and its stereoselective conversion into (+)-2,3-(isoprpylidenedioxy)-4-cyclopentenone, a versatile building block for the synthesis of cyclopentanoid natural products, have been described.

EFFICIENT ENANTIOSELECTIVE SYNTHESES OF CARBOCYCLIC NUCLEOSIDE AND PROSTAGLANDIN SYNTHONS

Simple and efficient enantioselective syntheses of two hydroxylated cyclopentenones, 2 and 10, which are useful intermediates for the synthesis of various carbocyclic nucleosides and prostaglandins, directly from readily available sugars are described.

Improved practical synthesis of a prostaglandin and carbocyclic nucleoside synthon

An efficient, four step synthesis of chiral enone 2a [(+)-2,3-(isopropylidenedioxy)-4-cyclopentenone] from diol 1a (X = Cl), available from microbial oxidation of chlorobenzene, is described. This synthesis is a vast improvement over that previously reported and compares very favorably with others in the literature.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

A short, concise synthesis of queuine

A short, concise synthesis of queuine was accomplished in a 36% overall yield through a convergent scheme utilizing a reductive amination as the penultimate step. The synthesis demonstrates the utility of silylation to facilitate reactions of various pyrrolo[2,3-d]pyrimidine intermediates, and offers the possibility of easily accessing related pyrrolo[2,3-d]pyrimidines as well as making additional analogues of queuine.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides methods of synthesizing the purified enantiomers of oleocanthal. The invention further provides methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.