105581-83-7

Upstream product

• 282550-80-5 (S)-4-isopropyl-3-((1S,2S)-2-methoxymethoxy-1-methylsulfanyl-2-phenyl-ethyl)-5,5-diphenyl-oxazolidin-2-one 
• 17199-29-0 (S)-Mandelic acid 
• 282551-79-5 (S)-8,8,9,9-tetramethyl-5-phenyl-2,4,7-trioxa-8-siladecane 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 282550-73-6 (S)-3-((1S,2S)-2-hydroxy-1-methylsulfanyl-2-phenyl-ethyl)-4-isopropyl-5,5-diphenyl-oxazolidin-2-one 
• 169220-96-6 (S)-methoxymethoxy-phenyl-acetic acid methyl ester 

Downstream Products

• 269401-74-3 (S)-2-methyloxymethoxy-2-phenyl-1-ethyl bromide 
• 269401-52-7 (S)-2-hydroxy-2-phenyl-ethylmethanethiosulfonate 
• 269401-76-5 (S)-2-methyloxymethoxy-2-phenyl-ethylmethanethiosulfonate 
• 1457952-42-9 (S)-(2-methoxy-1-(methoxymethoxy)ethyl)benzene 
• 65487-97-0 (S)-(+)-2-methoxy-1-phenylethanol 
• 1457952-46-3 (S)-2-methoxy-1-phenylethyl-1 H-imidazole-1-carboxylate 
• 1457952-48-5 (S)-2-methoxy-1-phenylethyl((S)-2-methoxy-2-phenylethyl) carbonate 
• 1457952-49-6 bis((S)-2-methoxy-1-phenylethyl) carbonate 
• 1457952-52-1 (R)-2-methoxy-1-phenylethyl((S)-2-methoxy-1-phenylethyl) carbonate 
• 269401-72-1 (S)-2-methyloxymethoxy-2-phenyl-1-ethylmethanesulfonate 

Relevant academic research and scientific papers

Microstructure analysis of a CO2 copolymer from styrene oxide at the diad level

A large amount of interesting information on the alternating copolymerization of CO2 with terminal epoxides has already been reported, such as the regiochemistry of epoxide ring-opening and the stereochemistry of the carbonate unit sequence in the polymer chain. Moreover, the microstructures of CO2 copolymers from propylene oxide and cyclohexene oxide have also been well-studied. However, the microstructure of the CO2 copolymer from styrene oxide (SO), an epoxide that contains an electron-withdrawing group, has not yet been investigated. Herein, we focus on the spectroscopic assignment of the CO2 copolymer from styrene oxide at the diad level by using three kinds of model dimer compounds, that is, T-T, H-T, and H-H. By comparing the signals in the carbonyl region, we concluded that the signals at δ=154.3, 153.8, and 153.3 ppm in the 13C NMR spectrum of poly(styrene carbonate) were due to tail-to-tail, head-to-tail, and head-to-head carbonate linkages, respectively. Moreover, various isotactic and syndiotactic model compounds based on T-T, H-T, and H-H (dimers (R,R)-T-T, (S,S)-T-T, and (R,S)-T-T; (R,R)-H-T, (S,S)-H-T, and (R,S)-H-T; (R,R)-H-H, (S,S)-H-H, and (R,S)-H-H) were synthesized for the further spectroscopic assignment of stereospecific poly(styrene carbonate)s. We found that the carbonate carbon signals were sensitive towards the stereocenters on adjacent styrene oxide ring-opening units. These discoveries were found to be well-matched to the microstructures of the stereoregular poly(styrene carbonate)s that were prepared by using a multichiral CoIII-based catalyst system. T-T races: The spectroscopic assignment of regio- and stereoregular poly(styrene carbonate)s at the diad level was performed by 13C NMR studies of three kinds of model compounds, as well as their syndiotactic (R,S) and isotactic (R,R or S,S) dimers. Copyright

Lithiated 4-isopropyl-3-(methylthiomethyl)-5,5-diphenyloxazolidin-2-one: A chiral formyl anion equivalent for enantioselective preparations of 1,2-diols, 2-amino alcohols, 2-hydroxy esters, and 4-hydroxy-2-alkenoates

The heterocyclic compound specified in the title (and readily prepared from commercial precursors) has a sterically protected C=O group, so that direct lithiation by BuLi at the exocyclic CH2 group is possible (3 → Li-3). The lithiated N,S-acetal derivative (Li-3) adds diastereoselectively to aldehydes (Table 2), unsymmetrical ketones (Table 3), chalcone (1,4-addition, Scheme 2), and N-phosphinoyl-and N-sulfonylimines (Table 4). Protection of the newly formed OH groups (Scheme 3) and/or MeS/OH displacement by Hg(O2CCF3)2 in aqueous THF/acetonitrile converts the N,S-acetals into hemiaminals (→ 20) which, in turn, are readily cleaved to aldehydes, with recovery of the chiral auxiliary (1, Scheme 4). The aldehydes (especially those lacking α-carbonyl hydrogens) may be isolated, or they are trapped in situ by reduction to (selectively protected) diols or amino alcohols, by addition of Grignard or Li reagents, which provides diols with two stereogenic centers, by oxidation to give 2-hydroxy esters, or by olefination to provide 4-hydroxy-2-alkenoates (Scheme 5). The scope and limitations of the new, overall enantioselective transformation are determined, and the readily recovered chiral auxiliary used is compared with oxazolidinones of other substitution patterns (Scheme 7). The configuration of a number of products has been assigned by single-crystal X-ray diffraction (cf. Figure 5). These structures and similarities of NMR data led to configurational assignment of the other products (see formulas in the schemes and tables) by analogy. A simple mechanistic model for the stereochemical course of the addition of Li-3 to aldehydes and ketones is presented (Figure 6).

Covalent modification of subtilisin Bacillus lentus Cysteine mutants with enantiomerically pure chiral auxiliaries causes remarkable changes in activity

Methanethiosulfonate reagents may be used to introduce virtually unlimited structural modifications in enzymes via reaction with the thiol group of cysteine. The covalent coupling of enantiomerically pure (R) and (S) chiral auxiliary methanethiosulfonate ligands to cysteine mutants of subtilisin Bacillus lentus induces spectacular changes in catalytic activity between diastereomeric enzymes. Amidase and esterase kinetic assays using a low substrate approximation were used to establish k(cat)/K(M) values for the chemically modified mutants, and up to 3-fold differences in activity were found between diastereomeric enzymes. Changing the length of the carbon chain linking the phenyl or benzyl oxazolidinone ligand to the mutant N62C by a methylene unit reverses which diastereomeric enzyme is more active. Similarly, changing from a phenyl to benzyl oxazolidinone ligand at S166C reverses which diastereomeric enzyme is more active. Chiral modifications at S166C and L217C give CMMs having both high esterase k(cat)/K(M)'s and high esterase to amidase ratios with large differences between diastereomeric enzymes. Copyright (C) 2000 Elsevier Science Ltd.

A Valine-Derived Lithiated 3-Methylthiomethyl-1,3-oxazolidin-2-one for Enantioselective Nucleophilic Hydroxymethylation, Formylation, and Alkoxycarbonylation of Aldehydes

(Equation Presented) The 3-methylthiomethyl-4-isopropyl-5,5-diphenyl-1,3-oxazolidin-2-one (I, prepared in three steps from Boc-valine ester) is lithiated and added to aldehydes, with protecting in situ trapping of the primary adducts, to give the N,S-acet

Asymmetric Synthesis of (5R,6S)-6-Acetoxy-5-hexadecanolide, the Major Component of the Oviposition Attractant Pheromone of the Mosquito Culex pipens fatigans, and Two of Its Stereoisomers

The benzyl derivatives of (R)- and (S)-2-hydroxydodecanal have been prepared by a previously described asymmetric synthesis based on a chiral 1,3-oxathiane and have been converted into (5R,6S)-6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone, and its 5R,6R and 5S,6R stereoisomers in highly diastereoselective fashion.The steps involved are Grignard addition of 5-pentenylmagnesium bromide, Mitsunobu inversion for one of the erythro (5R,6S) isomers and oxidation-hydride reduction for the other, ozonization, oxidation, lactone formation, debenzylation, and acetylation, the overall yield in these steps being 30-42percent.