64028-83-7

Upstream product

• 32464-98-5 (2S)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 109-92-2 ethyl vinyl ether 
• 184110-35-8 (2S,1'R/S)-Ethyl-2-(1'-ethoxyethoxy)propanoate 
• 184110-37-0 (2S,1'R/S)-2-(1'-Ethoxyethoxy)propan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 687-47-8 (S)-Ethyl lactate 

Downstream Products

• 16088-60-1 1-bromo-2(S)-hydroxypropane 
• 32464-98-5 (2S)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 61217-63-8 (S,S)-(+)-bis(2-hydroxypropyl) ether 

Relevant academic research and scientific papers

Novel synthesis of chiral, enantiomerically pure thiodiglycols and diglycols

Natural α-hydroxy acids have been converted in a sequence of O- protection, reduction, O-activation, thioether and ether formation and deprotection to chiral, non-racemic β,β'-dihydroxy thioethers 1a, 1b and ether 1c. Overall yields are excellent (75%). In an attempt to synthesize the respective dihydroxy ether 1d derived from mandelic acid 1,3-dioxolane derivatives 7 were obtained.

SYNTHESIS OF AN ORALLY ACTIVE PAF ANTAGONIST OF THE N-PENTADIENAMIDE CLASS

The PAF antagonist -5-(4-methoxyphenyl)-N--2,4-decadienamide (2) was synthesized from (S)-α-methyl-3-pyridinebutanol (14), which was obtained either from ethyl lactate or by enantioselective kinetic hydrolysis of its racemate using the lipase derived from Pseudomonas cepacia (syn.P. fluorescens).Mesylation of 14, followed by azide displacement and hydrogenation, produced amine (7), which was coupled with the p-nitrophenol ester (8) to give 2.The direct coupling of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid (27) with azide(24) in the presence of tri-n-butylphosphine also gave 2.Acid (27) was prepared by a vinylogous Reformatsky reaction between ketone (25) and methyl 4-bromocrotonate.

Access to (S)-2-Methyloxetane and the Precursor (S)-1,3-Butanediol of Hight Enantiomeric Purity

(S)-2-Methyloxetane (1) and its precursor (S)-1,3-butanediol (2) were prepared in low to moderate chemical yield with less than 0.5percent racemization from (S)-ethyl lactate (4) and from (2S,3S)-allothreonine (14b).For the first time the enantiomeric purities of both the starting material and the product (1) were carefully determined by high-precision capillary gas chromatography on optically active resolving stationary phases.The validity of the quadrant rule, correlating the relative configuration of alkyloxiranes with the order of elution from manganese(II) bis (3) by complexation gas chromatography, is also confirmed for 2-methyloxetane (1).

Synthesis of optically active 2s-, and 7s-methyl-1.6-dioxa-spiro[4.5] decane, the pheromone components of Paravespula vulgaris (L.), from S-ethyl lactate.

(-)-2S, 5RS-1 and (-]-7S, 5S-2 are obtained from S-ethyl lactate 4 and their absolute configuration is thus directly correlated. Accurate enantiomeric compositions of intermediates and products were measured by complexation gas chromatography on nickel-, and manganese-bis-3-heptafluorobutyryl-1R-camphorate, 3. It could be conclusively established that the syntheses proceed with a high degree of preservation of configuration.