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
• Article Data: 12

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

Description

ALPHA,BETA-ISOPROPYLIDENE-L-GLYCERIC ACID METHYL ESTER is a complex organic compound with a unique chemical structure. It is characterized by its chiral center and the presence of a methyl ester group. This molecule is derived from L-glyceric acid, which has been modified through the introduction of an isopropylidine group and a methyl ester group. Its specific structure endows it with potential applications in various fields.

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

• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 615-34-9 methyl glycerate 
• 77-76-9 2,2-dimethoxy-propane 
• 10303-88-5 methyl L-glycerate 
• 186581-53-3 diazomethane 
• 102045-96-5 2,3-O-isopropylidene-L-glyceric acid 
• 117205-81-9 potassium (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 74-88-4 methyl iodide 
• 67-64-1 acetone 
• 473-81-4 (S)-glyceric acid 
• 115114-86-8 3,4-O-isopropylidene-L-(S)-erythrulose 
• 116-11-0 2-Methoxypropene 
• 108865-84-5 methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 67-56-1 methanol 

Downstream Products

• 349648-25-5 (S)-4-((R)-1-Benzyloxy-1-ethynyl-allyl)-2,2-dimethyl-[1,3]dioxolane 
• 349648-27-7 (R)-2-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-undec-3-ynal 
• 349648-26-6 (S)-4-((R)-1-Benzyloxy-1-vinyl-dec-2-ynyl)-2,2-dimethyl-[1,3]dioxolane 
• 117205-81-9 potassium (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 16975-61-4 (R)-2,2-dimethyl-4-trityloximethyl-[1,3]dioxolane 
• 192506-88-0 C₁₃H₁₇NO₃ 
• 186521-82-4 (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)acetylene 
• 86562-71-2 2-<(S)-2,2-dimethyl-1,3-dioxolane-4-yl>-2-propanol 
• 121701-23-3 (R,Z)-[(2,2-dimethyl-1,3-dioxolan-4-yl)methylene]-N-benzylamine N-oxide 
• 56017-85-7 (S)-4-ethynyl-2,2-dimethyl-1,3-dioxolane 
• 1219030-95-1 [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](3-[(4-methoxybenzyl)oxy]methyl-5,6-dihydro-1,4-dithiin-2-yl)methanone 
• 99566-52-6 (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanone 

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.

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.

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.