81036-97-7

Usage

Uses

Used in Pharmaceutical Industry:
(2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one is utilized as a chiral building block for the synthesis of various pharmaceuticals. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which is crucial for the development of drugs with specific therapeutic effects and minimal side effects.
Used in Agrochemical Industry:
In the agrochemical sector, (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one is employed as a chiral building block for the synthesis of agrochemicals. (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one's ability to produce enantiomerically pure products ensures the development of effective and targeted agrochemicals with reduced environmental impact.
Used in Asymmetric Catalysis:
(2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one also serves as a chiral ligand in metal-catalyzed asymmetric reactions. Its (2S,5S) configuration imparts specific reactivity and selectivity, facilitating the synthesis of enantiomerically pure compounds with high yields and selectivity, which is vital for the production of complex organic molecules with precise stereochemistry.

Upstream product

• 17199-29-0 (S)-Mandelic acid 
• 630-19-3 pivalaldehyde 
• 62617-39-4 1,1-dimethoxy-2,2-dimethylpropane 
• 611-71-2 MANDELIC ACID 
• 78804-02-1 (+/-)-trimethylsilyl 2-<(trimethylsilyl)oxy>-2-phenylethanoate 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 120-92-3 cyclopentanone 

Downstream Products

• 81037-00-5 (2S,5S)-2-(t-butyl)-5-phenyl-5-propyl-1,3-dioxolan-4-one 
• 81036-98-8 (S)-2-tert-Butyl-5-methyl-5-phenyl-[1,3]dioxolan-4-one 
• 81036-98-8 (2S,5S)-2-tert-butyl-5-methyl-5-phenyl-1,3-dioxolane-4-one 
• 81037-01-6 (2S,5R)-2-tert-Butyl-5-methyl-5-phenyl-[1,3]dioxolan-4-one 
• 195388-29-5 (3R,4S)-3-hydroxy-1,3,4-triphenylazetidin-2-one 
• 195388-30-8 (3R,4R)-3-Hydroxy-1,3,4-triphenyl-azetidin-2-one 
• 81036-99-9 (S)-5-Allyl-2-tert-butyl-5-phenyl-[1,3]dioxolan-4-one 
• 81037-00-5 (S)-2-tert-Butyl-5-phenyl-5-propyl-[1,3]dioxolan-4-one 
• 302842-80-4 (2S,5R)-2-(tert-butyl)-5-phenyl-5-(1-hydroxycyclopentyl)-1,3-dioxolan-4-one 
• 654068-37-8 (2S,5R)-2-tert-butyl-5-(4-nitrophenyl)-5-phenyl-1,3-dioxolan-4-one 

Relevant academic research and scientific papers

Practical and robust method for the preparation of Seebach and Frater's chiral template, cis-2-substituted 5-methyl(or phenyl)-1,3-dioxolan-4-ones

A practical and highly stereoselective method for the preparation of three cis-2-substituted 5-methyl (orphenyl)-1,3-dioxolan-4-ones 3a and 7a (Seebach and Frater's chiral template), and a new modified analogue 7b has been developed. The present robust me

Convenient synthesis of O-functionalized mandelic acids via Lewis acid mediated transformation of 1,3-dioxolan-4-ones

An efficient method for the synthesis of O-substituted mandelic acids containing alkenyl, alkynyl, methoxycarbonyl, or phenacyl fragments via the Lewis acid-catalyzed reaction of 1,3-dioxolan-4-ones with different C-nucleophiles is proposed.

Discovery of a Novel Muscarinic Receptor PET Radioligand with Rapid Kinetics in the Monkey Brain

Positron emission tomography (PET), together with a suitable radioligand, is one of the more prominent methods for measuring changes in synaptic neurotransmitter concentrations in vivo. The radioligand of choice for such measurements on the cholinergic sy

Practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones and highly diastereoselective cis-2,5-disubstituted 1,3-dioxolane-4-ones from α-hydroxy acids catalyzed by N-triflylphosphoramide

N-triflylphosphoramide (NTPA) was found to be an efficient Br?nsted acid catalyst for the practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones. Racemic and optically pure mandelic acid and lactic acid could be protected using several aldehydes in

An efficient synthetic approach towards fully functionalized tetronic acids: The use of 1,3-dioxolane-2,4-diones as novel protected-activated synthons of α-hydroxy acids

A new strategy for the synthesis of tetronic acids with control over the regioselective introduction of substituents at the C-5 position has been developed. The construction of the densely functionalized quaternary carbon center within these molecules is of great importance. The key element for the proposed protocol was the utilization of O-carboxyanhydrides (OCA's) of optically active α-hydroxy acids, as promising bidentate protective/activating precursors. The structure of the new compounds was investigated by using NMR spectral data and X-ray structural analyses.

Stereoisomers of N-substituted soft anticholinergics and their zwitterionic metabolite based on glycopyrrolate - Syntheses and pharmacological evaluations

Purpose. In this study, isomers of two N-substituted soft anticholinergics based on glycopyrrolate, SGM (PcPOAGP_NA.Me) and SGE (PcPOAGP_NA.Et) [3′-(2-cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1′-methyl-1′- alkoxycarbonylpyrrolidinium bromide] and their zwitterionic metabolite, SGa (PcPOAGP_NA.H) [3′-(2-cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1′- methyl-1′-carboxymethylpyrrolidinium inner salt] were synthesized and their pharmacological activities were evaluated in vitro and in vivo. Methods. The isomers of SGM and SGE were synthesized with both optically pure methyl-cyclopentylmandelate and 3-hydroxy-N-methylpyrrolidine. Trans-esterification followed by quarternization with alkyl bromoacetate gave four isomers of SGM or SGE with the nitrogen chiral center unresolved (2R3′S-SGM, 2R3′R-SGM, 2S3′S-SGM, 2S3′R-SGM or 2R3′S-SGE, 2R3′R-SGE, 2S3′S-SGE, 2S3′R-SGE). The hydrolysis of these four isomers followed by HPLC separation resulted in eight fully resolved isomers of SGa (2R3′R1′R, 2R3′S1′R, 2R3′R1′S, 2R3′S1′S, 2S3′R1′R, 2S3′S1′R, 2S3′R1′S, and 2S3′S1′S). Pharmacological activities were assessed by using in vitro receptor-binding assay and guinea pig ileum pA2-assay, and by evaluating the in vivo rabbit mydriatic effects. Results were compared to those obtained with conventional anticholinergic agents, such as glycopyrrolate, N-meythylscopolamine, and tropicamide, as well as those obtained with previously prepared racemic mixtures and 2R isomers. Results. Receptor binding pK i values at cloned human muscarinic receptors (M1-M 4 subtypes) were in the 6.0-9.5 range for the newly synthesized SGM and SGE isomers, and in the 5.0-8.6 range for the SGa isomers. In all cases, 2R isomers were significantly more active than 2S isomers (27 to 447 times for SGM isomers, and 6 to 4467 times for SGa isomers). Among the four SGM isomers with unresolved 1′ (N) chiral center, the 3′R isomers were more active than the corresponding 3′S isomers (1.5-12.9 times), whereas, among the SGa isomers, the 3′S isomers were not always more active than the corresponding 3′R isomers indicating that activity determined based on configuration at chiral center 3′ is significantly affected by the configuration of the other two chiral centers, 2 and 1′. Among the completely resolved eight SGa isomers (all three chiral centers resolved), 1′S isomers were always more active than the corresponding 1′R isomers (1.8-22.4 times). Results also indicate that some isomers showed good M3/M2 muscarinic-receptor subtype-selectivity (about 3-5 times), and 2R and 3′S were the determining configurations for this property. Guinea pig ileum assays and rabbit mydriasis tests on SGa isomers further confirmed the stereospecificity. In rabbit eyes, some 2R-SGa isomers showed mydriatic potencies similar to glycopyrrolate and exceeded tropicamide, but their mydriatic effects lasted considerably shorter, and they did not induce dilation of the pupil in the contralateral, water-treated eye. These results indicate that these compounds are locally active, but safe and have a low potential to cause systemic side effects. The pharmacological potency of the eight SGa isomers was estimated as 2R3′S1′S ≈ 2R3′R1′S ≈ 2R3′S1′R > 2R3′R1′R > 2S3′R1′S > 2S3′S1′S ≈ 2S3′R1′R > 2S3′S1′R (p 3/M2 muscarinic-receptor subtype-selectivity of soft anticholinergics, SGM, SGE, and SGa have been demonstrated. In agreement with previous results, the potential for their effective and safe use has been confirmed.

SOFT ANTICHOLINERGIC ESTERS

Soft anticholinergic esters of the formulas: wherein R1 and R2 are both phenyl or one of R1 and R2 is phenyl and the other is cyclopentyl; R is C1-C8 alkyl, straight or branched chain; and X- is an anion with a single negative charge; and wherein each asterisk marks a chiral center; said compound having the R, S or RS stereoisomeric configuration at each chiral center unless specified otherwise, or being a mixture thereof.

Stereoselective synthesis of the optical isomers of a new muscarinic receptor antagonist, quinuclidin-3-yl 2-(cyclopent-1-enyl)-2-hydroxy-2- phenylacetate

The enantiopure isomers of a new muscarinic receptor antagonist, quinuclidin-3-yl 2-(cyclopent-1-enyl)-2-hydroxy-2-phenylacetate were synthesised by a practical stereoselective synthetic method, using pivaldehyde as steric hindrance agent from the chiral starting material, (S) or (R)-mandelic acid. The isomers were obtained with 72-78% yields in 98-99% e.e.

Stereoselective synthesis of the optical isomers of a new muscarinic receptor antagonist, HL-031120

We present here a practical stereoselective synthetic method to produce enantiopure isomers of a new muscarinic receptor antagonist, HL-031120 (3-quinuclidinyl-2′-cyclopentyl-2′-hydroxy-2′-phenylacetate, I). Four optical isomers were effectively by stereoselective synthesized using pivaldehyde as steric hindrance agent from the chiral starting material, ( S ) or ( R )-mandelic acid. The isomers were obtained with 70-76% yields in 98-99% e.e. Copyright Taylor & Francis Group, LLC.

Stereoselective synthesis of 3-azabicyclo[3,3,1]nonan-9α-yl α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate hydrochloride

The isomers of α-(cyclopentyl-1-ene)-α-hydroxy-α- phenylacetic acid esters derived from 3-azabicyclo[3,3,1]nonan-9α-ol ((R)-1 and (S)-1) were obtained in high enantiomeric excess by effective stereoselective synthesis from the chiral starting material, (S