91191-95-6

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-2-(METHYLMETHOXY)-1,2-PROPANEDIOL is used as a chiral building block for the synthesis of enantiomerically pure pharmaceuticals. Its ability to selectively generate pure enantiomers is crucial for producing drugs with targeted therapeutic effects and reduced side effects, ensuring the safety and efficacy of medications.
Used in Agrochemical Industry:
(S)-MMPD is employed as a chiral building block in the synthesis of agrochemicals, contributing to the development of effective and environmentally friendly pesticides and herbicides. The enantioselective synthesis facilitated by (S)-MMPD allows for the creation of agrochemicals with improved performance and reduced impact on non-target organisms.
Used in Asymmetric Synthesis:
(S)-(+)-2-(METHYLMETHOXY)-1,2-PROPANEDIOL is used as a chiral ligand and catalyst in asymmetric synthesis, a technique that enables the production of enantiomerically pure compounds. Its application in this field is instrumental in the development of novel chiral molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Material Science:
(S)-MMPD has potential applications in the development of new materials, leveraging its chiral properties to create materials with unique physical and chemical characteristics. This can lead to the discovery of innovative materials with applications in various fields, such as nanotechnology, polymer science, and advanced materials for specific industrial uses.
Used in Organic Chemistry Research:
(S)-(+)-2-(METHYLMETHOXY)-1,2-PROPANEDIOL is utilized as a valuable tool in organic chemistry research, particularly in the study of chiral compounds and their interactions. Its use in research helps to advance the understanding of chirality and its implications in chemical reactions and molecular structures, paving the way for new discoveries and applications in the field of organic chemistry.

InChI:InChI=1/C5H12O3/c1-5(3-6)8-4-7-2/h5-6H,3-4H2,1-2H3/t5-/m0/s1

Upstream product

• 119650-35-0 (S)-methyl 2-(methoxymethoxy)propanoate 
• 91191-93-4 (-)-ethyl (S)-2-hydroxypropionate methoxymethyl ether 

Downstream Products

• 1147133-24-1 C₁₂H₁₅NO₇ 
• 1311285-25-2 N-[(2Z)-1-butyl[1,3]thiazolo[5,4-b]pyridin-2(1H)-ylidene]-2-{[(2S)-2-(methoxymethoxy)propyl]oxy}-5-(trifluoromethyl)benzamide 
• 1311285-22-9 N-[(2Z)-3-butyl[1,3]thiazolo[4,5-c]pyridin-2(3H)-ylidene]-2-{[(2S)-2-(methoxymethoxy)propyl]oxy}-5-(trifluoromethyl)benzamide 

Relevant academic research and scientific papers

Stereoselective synthesis of (-)-synparvolide B

The stereoselective synthesis of (-)-synparvolide B, isolated from Syncolostemon parviflorus, has been accomplished from (S)-ethyl lactate. A 1,2-chelation controlled allylation, Sharpless asymmetric epoxidation, Brown asymmetric allylation and RCM reactions were used as the key steps.

Chiral tetraphenylethenes as novel dopants for calamitic and discotic liquid crystals

Three series of novel chiral tetraphenylethenes have been prepared: citronellyl-derived ethers 1a, b, lactate-derived ethers 2d, g, h, i and lactate-derived esters 3a-c, e-h. Helical twisting powers (HTPs) were determined for those derivatives of 1-3, whi

Scope and limitations of ether-directed, metal-catalysed aza-Claisen rearrangements; Improved stereoselectivity using non-coordinating solvents

In an effort to understand and enhance the stereochemical outcome of the MOM-ether directed rearrangement of allylic trichloroacetimidates we have investigated various reaction conditions for this process. A range of Pd(ii) and other metal catalysts have been shown to effectively catalyse the rearrangement providing the subsequent allylic amides in high selectivity (up to 11: 1 ratio of diastereomers). The replacement of THF as a solvent in this reaction with non-coordinating solvents such as toluene has led to an enhancement of the directing effect resulting in a significant increase in the diastereoselective outcome (15: 1 ratio). The reaction was also carried out for the first time, using a highly coordinating ionic solvent which disrupts binding of the Pd(ii)-catalyst to the MOM-ether yielding the allylic amide in only moderate diastereoselectivity. These results provide further evidence for the ether directed aza-Claisen rearrangement of allylic trichloroacetimidates. The Royal Society of Chemistry 2006.

Stereoselective β-hydroxy-α-amino acid synthesis via an ether-directed, palladium-catalysed aza-Claisen rearrangement

A highly diastereoselective synthesis of (2S,3S)-β-hydroxy-α- amino acids has been developed from enantiopure α-hydroxy acids using a MOM-ether-directed, palladium(II)-catalysed, aza-Claisen rearrangement of allylic acetimidates to effect the key step. This highly stereoselective process gave allylic amides in diastereomeric ratios of up to 14 : 1. Problems associated with the isolation of 1,3-products (anti-Claisen) from sterically demanding substrates via an in situ palladium(0)-catalysed rearrangement process were overcome by the addition of a re-oxidant, p-benzoquinone, leading to cleaner reactions and improved yields of the 3,3-products (Claisen). The target β-hydroxy-α-amino acids are an important class of natural products that are also components of more complex organic compounds with significant biological properties. The Royal Society of Chemistry 2005.

A highly stereoselective ether directed palladium catalysed aza-Claisen rearrangement

A highly stereoselective rearrangement of allylic trichloroacetimidates to allylic trichloroamides has been achieved using adjacent ether groups to direct facial coordination of the palladium(II) catalyst. The Royal Society of Chemistry 2005.

ALLYLIC ORGANOMETALLIC WAY TO CONTROL ACYCLIC STEREOCHEMISTRY AND ITS APPLICATION TO THE SYNTHESIS OF CARBOHYDRATES

The Cram/anti-Cram selectivity in the reactions of allylmetals with aldehydes and the erythro/threo selectivity in the reactions of substituted allylic organometallic compounds with other aldehydes can be controlled by the metal (M).Based on both selectiv

High Diastereoface Selection in an Ester Enolate Addition to α-Alkoxy Aldehydes: Stereoselective Synthesis of α-Methylene-β-hydroxy-γ-alkoxy Esters

The aldol-type condensation of β-(dimethylamino)propionates 3 and 4 with a series of α-alkoxy aldehydes proceeds with unprecedented high stereoselectivity (up to 24:1) to give anti α-methylene-β-hydroxy-γ-alkoxy esters.The best results were obtained when the reaction was carried out in diethyl ether and the ester enolate was allowed to equilibrate to the thermodynamically more stable geometric isomer.