60456-21-5

Basic information

• Product Name: ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER
• Synonyms: ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER;METHYL 2,3-O-ISOPROPYLIDENE-L-GLYCERATE;METHYL ALPHA, BETA-ISOPROPYLIDENE-L-GLYCERATE;METHYL (S)-(-)2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLATE;METHYL (S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLATE;α,β-isopropylidene-l-glyceric acid methyl ester;(S)-2,2-Dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester;Methyl α,β-isopropylidene-L-glycerate, Methyl 2,3-O-isopropylidene-L-glycerate, α,β-Isopropylidene-L-glyceric acid methyl ester
• CAS NO: 60456-21-5
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• Product Categories: pharmacetical
• Mol File: 60456-21-5.mol

Chemical Properties

• Boiling Point: 84-86 °C15 mm Hg(lit.)
• Flash Point: 78°C
• Appearance: /
• Density: 1.106 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.404mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• Storage Temp.: 2-8°C
• BRN: 4292352
• CAS DataBase Reference: ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER(60456-21-5)
• EPA Substance Registry System: ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER(60456-21-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 60456-21-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER is used as a chiral building block for the synthesis of complex organic molecules, particularly in the development of pharmaceutical compounds. Its unique structure and chiral center make it a valuable component in the creation of new drugs with specific biological activities.
Used in Chemical Synthesis:
ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER is used as a starting material for the preparation of various organic compounds, such as enediones and cyclopentenone derivatives. These compounds can be further utilized in the synthesis of other complex molecules, including those with potential applications in the pharmaceutical, agrochemical, and materials science industries.
Used in Bacterial Communication:
ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER is used as a starting material for the preparation of (S)-4,5-dihydroxy-2,3-pentanedione (DPD), a precursor for autoinducer (AI)-2 in bacteria. AI-2 is a signaling molecule involved in quorum sensing, a communication mechanism used by bacteria to coordinate their behavior based on population density. This application highlights the potential of ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER in the study and manipulation of bacterial communication pathways.

InChI:InChI=1/C7H12O4/c1-7(2)10-4-5(11-7)6(8)9-3/h5H,4H2,1-3H3/t5-/m0/s1

Upstream product

• 67-56-1 methanol 
• 121357-95-7 (3R,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-dihydro-furan-2-one 
• 108865-84-5 methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 116-11-0 2-Methoxypropene 
• 10303-88-5 methyl L-glycerate 
• 115114-86-8 3,4-O-isopropylidene-L-(S)-erythrulose 
• 473-81-4 (S)-glyceric acid 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 117205-81-9 potassium (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 102045-96-5 2,3-O-isopropylidene-L-glyceric acid 
• 615-34-9 methyl glycerate 

Downstream Products

• 55032-26-3 (R)-2,3-dihydroxy-N-(4-vinyl-phenethyl)-propionamide 
• 86562-71-2 2-<(S)-2,2-dimethyl-1,3-dioxolane-4-yl>-2-propanol 
• 10303-88-5 methyl L-glycerate 
• 61821-86-1 (R)-2,2-dimethyl-1,3-dioxolan-4-yl methyl ketone 
• 99566-52-6 (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanone 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 102045-96-5 2,3-O-isopropylidene-L-glyceric acid 
• 67-56-1 methanol 
• 114746-70-2 (R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 930795-32-7 (1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile 
• 930795-33-8 (1'R,2'S,4''R)-3-[4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-1'-(1'''-hydroxyallyl)-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile 
• 930795-39-4 1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)allyl acetate 
• 930795-42-9 acetic acid 1-[1-(2-cyano-ethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-3-methyl-cyclohex-3-enyl]-5-[3-methyl-5-(3-triisopropylsilanyloxy-propyl)-tetrahydro-furan-2-yl]-hex-4-enyl ester 
• 930795-41-8 (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate 

Relevant articles and documents

Synthesis of Phosphatidylserine and Its Stereoisomers: Their Role in Activation of Blood Coagulation

Natural phosphatidylserine (PS), which contains two chiral centers, enhances blood coagulation. However, the process by which PS enhanced blood coagulation is not completely understood. An efficient and flexible synthetic route has been developed to synthesize all of the possible stereoisomers of PS. In this study, we examined the role of PS chiral centers in modulating the activity of the tissue factor (TF)-factor VIIa coagulation initiation complex. Full length TF was relipidated with phosphatidylcholine, and the synthesized PS isomers were individually used to estimate the procoagulant activity of the TF-FVIIa complex via a FXa generation assay. The results revealed that the initiation complex activity was stereoselective and had increased sensitivity to the configuration of the PS glycerol backbone due to optimal protein-lipid interactions.

Practical one-pot synthesis of protected l-glyceraldehyde derivatives

A large-scale, simple, economic, and safe procedure for the preparation of l-glyceraldehyde acetonide under conditions, which allow its direct transformation (one-pot) into the desired products (acetylene, imine, nitrone, unsaturated ester) is reported. l-Glyceraldehyde acetonide is obtained from the corresponding ester, which is readily available from l-serine. Georg Thieme Verlag Stuttgart New York.

d- and l-Serine, useful synthons for the synthesis of 24-hydroxyvitamin D3 metabolites. A formal synthesis of 1α,24R,25-(OH)3-D3, 24R,25-(OH)2-D3 and 24S,25-(OH)2-D3

d- and l-Serine have been used for the enantioselective synthesis of tosylates 7a and 7b, useful building blocks for the synthesis of triols 5a and 5b which have already been obtained via a diastereoselective synthesis and used for the synthesis of 2a, 2b and 2c. We have thus performed a formal synthesis of 24S,25-(OH)2-D3, 24R,25-(OH)2-D3 and 1α,24R,25-(OH)3-D3.

Hydrolytic kinetic resolution of epoxides catalyzed by chromium(III)-endo, endo-2,5-diaminonorbornane-salen [Cr(III)-DIANANE-salen] complexes. Improved activity, low catalyst loading

The hydrolytic kinetic resolution (HKR) of terminal epoxides, using chiral chromium(III)-salen catalysts based on DIANANE (endo,endo-2,5-diaminonorbornane) , was studied. A broad substrate scope was found for the chromium(III)-DIANANE catalysts, and very low loadings (down to 0.05 mol%) were needed to achieve high enantiomeric purities of both the remaining epoxides and the product diols (up to >99% ee). Besides monosubstituted epoxides, 2-methyl-2-n-pentyloxirane, which is an example for 2,2-disubstituted epoxides, could be ring-opened in an asymmetric fashion with water in the presence of an electronically tuned chromium-(III)-DIANANE complex.

Synthesis of (S)-1-(1H-indol-4-yloxy)-3[4-(3-methoxyphenyl)-4- hydroxypiperidin-1-yl]-propan-2-ol (LY333068) succinate, and its 3-[14C]- isotopomer based on chiral glycerol-[14C] derivatives

The 3-[14C]-isotopomer of (S)-1-(1H-indol-4-yloxy)-3-[4-(3- methoxyphenyl)-4-hydroxypiperidin-1-yl]-propan-2-ol (LY333068), a 5HT(1A) antagonist, was prepared in 10 steps and 8.2% radiochemical yield from (L)- serine-[3-14C]. Deamination, esterification, and protection of the resulting diol gave methyl (R)2,2-dimethyl-1,3-dioxolane-4-carboxylate-[3- 14C], as a chiral and radiolabeled building block, which then was subsequently coupled with 4-hydroxyindole and 4-(3-methoxyphenyl)-4- hydroxypiperidine to give the titled product with 99.4% radiochemical purity.

Asymmetric synthesis of RK-682 and its analogs, and evaluation of their protein phosphatase inhibitory activities

We report an asymmetric synthesis of a potent tyrosine phosphatase inhibitor, RK-682 and its analogs. The absolute stereochemistry of RK-682 was determined to be (R). The inhibitory activities of RK-682 and its analogs, (R)-1a, (S)-1a, (R)-1b and (R)-1c toward various protein phosphatases (VHR, cdc25A, cdc25B, and PPI) are also reported.

Enzymes in Organic Synthesis, 15. Synthesis of Methyl (S)-(-)-2,3-O-Isopropylideneglycerate by Enantioselective Enzyme-Catalyzed Hydrolysis of Methyl (+/-)-2,3-O-Isopropylideneglycerate

In contrast to porcine pancreatic lipase (PPL), the serine proteases aP 41 and thermitase are suited as catalysts for the enantioselective ester hydrolysis of methyl (+/-)-2,3-O-isopropylideneglycerate (rac-1).These enzymes allow the preparation of methyl (S)-(-)-2,3-O-isopropylideneglycerate (1) with an enantiomeric excess of 84-87percent in a yield of 19-27percent related to the starting racemate. Key Words: Enzymes / Proteases / Ester hydrolysis, enzymatic / Isopropylideneglycerates / Resolution, kinetic / Glycerates

Oxidative Cleavage of Vicinal Diols at the Nickel Hydroxide Electrode

Vicinal diols are oxidatively cleaved with good yields by electrolysis at an oxide covered nickel electrode in an aqueous alkaline electrolyte and an undivided cell.The method is applied in the synthesis of optical pure derivatives of 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid.

Convenient One-Pot Conversion of Alcohols into Esters via Hemiacetal Intermediates

A simple and efficient one-pot oxidative procedure, adaptable to a large scale, is described for the preparation of methyl esters from either primary alcohols or vic-diols.The aldehyde is generated by Swern or periodate oxidation, followed by bromine oxidation of the methyl hemiacetal formed in aqueous methanolic solution.

L-(S)-ERYTHRULOSE A NOVEL PRECURSOR TO L-2,3-O-ISOPROPYLIDENE-C3 CHIRONS

Starting from L-(S)-erythrulose, now available in larger quantities, the preparation of L-(S)-glyceraldehyde, L-(R)-glycerol and L-(S)-methyl glycerate acetonides, via the protected L-(S)-3,4-O-isopropylideneerythrulose, is described.