356048-02-7

Basic information

• Product Name: (4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester
• Synonyms: (4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester;Methyl 1,3-Dioxo-4-methyl-2-oxo-2-thiolane-4-carboxylate
• CAS NO: 356048-02-7
• Molecular Formula: C₅H₈O₅S
• Molecular Weight: 180.18
• Product Categories: Heterocyclic Compounds;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 356048-02-7.mol

Chemical Properties

• Boiling Point: 237.367°C at 760 mmHg
• Flash Point: 97.356°C
• Appearance: /
• Density: 1.501g/cm³
• Vapor Pressure: 0.045mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: Refrigerator
• Solubility: Acetone, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: (4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester(356048-02-7)
• EPA Substance Registry System: (4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester(356048-02-7)

Safety Data

• Hazardous Substances Data: 356048-02-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a wide range of chemical reactions, such as esterification, amidation, and condensation, which are essential for the formation of complex molecules. This makes it a valuable tool for chemists working in the field of organic synthesis.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester is used as a building block for the development of new drugs. Its ability to form a variety of chemical bonds and its compatibility with other molecules make it an ideal candidate for the synthesis of drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
(4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester also finds application in the agrochemical industry, where it is used in the synthesis of various agrochemical products, such as pesticides and herbicides. Its reactivity and versatility enable the development of new and more effective compounds to protect crops and control pests.
Used in Material Science:
In the field of material science, (4S)-4-Methyl-2-oxo-[1,3,2]dioxathiolane-4-carboxylic Acid Methyl Ester is utilized in the development of new materials with specific properties. Its ability to form stable chemical bonds and its compatibility with other molecules make it a valuable component in the synthesis of advanced materials with applications in various industries, such as electronics, automotive, and aerospace.

InChI:InChI=1/C5H8O5S/c1-5(4(6)8-2)3-9-11(7)10-5/h3H2,1-2H3

Upstream product

• 147501-89-1 (R)-2,3-dihydroxy-2-methyl-propionic acid methyl ester 
• 147501-85-7 (S)-2,3-dihydroxy-2-methyl-propionic acid methyl ester 

Downstream Products

• 549504-45-2 (R)-3-Azido-2-hydroxy-2-methyl-propionic acid methyl ester 
• 356048-04-9 (R)-2-azido-3-hydroxy-2-methyl-propionic acid methyl ester 
• 549504-45-2 (S)-3-Azido-2-hydroxy-2-methyl-propionic acid methyl ester 

Relevant articles and documents

Understanding the unusual regioselectivity in the nucleophilic ring-opening reactions of gem-disubstituted cyclic sulfates. Experimental and theoretical studies

The regioselectivity of the nucleophilic ring-opening reactions of three gem-disubstituted cyclic sulfates with sodium azide has been studied from both experimental and theoretical viewpoints. It is found that, depending on the substituent present in the cyclic sulfate, the reaction displays reversed regioselectivity, which allows one or another regioisomer to be obtained with selectivities greater than 4:1. The theoretical calculations show that, contrary to previous understanding, the intrinsic preference in all cases is azide attack at the less-substituted Cβ position, a consequence of similar stereoelectronic effects in the three sulfates considered. The observed preference for Cα attack in the case of the ester sulfate is explained in terms of differential solvent effects, which are in turn due to subtle differences in the charge transfer in the different transition structures.

Enantioselective synthesis of α-methyl-D-cysteine and lanthionine building blocks via α-methyl-d-serine-β-lactone

(Matrix presented) We report here the enantioselective synthesis of Boc-α-methyl-D-cysteine(PMB)-OH and lanthionine building blocks through the regioselective ring opening of key intermediate Boc-α -methyl-D-serine-β-lactone.

Enantioselective synthesis of (S)- and (R)-α-methylserines: Application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

This report describes the synthesis of enantiomerically pure (S)- and (R)-α-methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary α-amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinal building blocks.