54656-65-4

Upstream product

• 67-56-1 methanol 
• 20047-41-0 (2R)-methyl 2-bromopropionate 
• 124-41-4 sodium methylate 
• 79-33-4 L-Lactic acid 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 
• 27871-49-4 (S)-Methyl lactate 

Downstream Products

• 23953-00-6 (S)-2-methoxypropanoic acid 

Relevant academic research and scientific papers

Conformational Study of Chiral Alkenes: The Influence of Protective Groups on the Relative Stability of Ground-State Rotational Isomers

A variable temperature NMR study shows that a protective group on the hydroxy function of a chiral allylic alcohol can either enhance or counter the influence of the vinyl substituent on the ground-state (GS) conformations.If the allylic hydroxy is protected as a methyl ether, the CH-eclipsed form I becomes favored to a greater degree for normal chiral alkenes.Furthermore, conformer I becomes preferred even for the γ-hydroxy-α,β-unsaturated esters, which normally favor the CO-eclipsed form (II).On the other hand, the tert-butyldimethylsilyl (TBDMS) ether enhances the preference for conformer II for the γ-hydroxy-α,β-unsaturated esters and diminishes the preference for the CH-eclipsed form of normal chiral alkenes.These facts are explained by the size of the allylic oxygen lone pairs.

Hydrophilic Oligo(lactic acid)s Captured by a Hydrophobic Polyaromatic Cavity in Water

Biologically relevant hydrophilic molecules rarely interact with hydrophobic compounds and surfaces in water owing to effective hydration. Nevertheless, herein we report that the hydrophobic cavity of a polyaromatic capsule, formed through coordination-driven self-assembly, can encapsulate hydrophilic oligo(lactic acid)s in water with relatively high binding constants (up to Ka=3×105 m?1). X-ray crystallographic and ITC analyses revealed that the unusual host–guest behavior is caused by enthalpic stabilization through multiple CH–π and hydrogen-bonding interactions. The polyaromatic cavity stabilizes hydrolyzable cyclic di(lactic acid) and captures tetra(lactic acid) preferentially from a mixture of oligo(lactic acid)s even in water.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.

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

Ether-directed diastereoselectivity in catalysed Overman rearrangement: comparative studies of metal catalysts

Ether-directed diastereoselectivity in Overman rearrangement of δ-methoxy and δ-TBDMSO substituted allylic trichloroacetimidates has been explored using PtCl2, PtCl4, AuCl and AuCl3 catalysts in comparison with commonly us

The efficient synthesis of alkoxy-esters from hydroxy carboxylic acids using dimsyllithium in dimethylsulfoxide followed by alkylation with an alkyl halide

Hydroxy acids are converted directly into the related alkyl ether-alkyl esters in high yields in a single operation by double deprotonation using dimsyllithium in dimethylsulfoxide followed by treatment with an alkyl halide.