61217-63-8

Upstream product

• 79-33-4 L-Lactic acid 
• 76946-21-9 (2S)-2-(tetrahydro-2H-pyran-2-yloxy)propan-1-ol 
• 42274-61-3 (2S)-2-(tetrahydro-2H-pyran-2-yloxy)propyl 4-methylbenzenesulfonate 
• 184110-37-0 (2S,1'R/S)-2-(1'-Ethoxyethoxy)propan-1-ol 
• 64028-83-7 (S)-1-tosyl-2-(1-ethoxyethoxy)propane 
• 297749-54-3 (S,S)-(-)-bis(2-benzyloxy-1-propyl) ether 
• 76946-24-2 C₁₆H₃₀O₅ 

Downstream Products

• 102421-33-0 (4S,8S)-4,8-dimethyl-3,6,9-trioxaundecane-1,11-diol dimesylate 
• 231611-10-2 (S,S)-(-)-bis<2-(p-tolylsulfonyloxy)propyl>ether 
• 76900-35-1 (2S,6S)-(+)-2,6-dimethyl-1,4,7,10,13-pentaoxacyclopentadecane 

Relevant academic research and scientific papers

One-Pot Generation and Conversion of Trichloroacetimidates for the Racemization-Free Allylation and Benzylation of α-Hydroxyesters and the Enantiopure Synthesis of a Chiral Diglycole

Ο-Allylations and Ο-benzylations of α-hydroxy esters (3a-3c) are performed without racemization. The reagents applied, Ο-allyl- and Ο-benzyltrichloroacetimidate (5a, 5b) are prepared and converted in a one-pot-procedure. After protection by benzylation (S)-(-)-ethyl lactate (3a) is converted by a sequence of carbonyl reduction, alcohol activation, ether formation, and deprotection to the optically active diglycole derivative 1a.

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.

Circular Dichroism Studies on Three Isomeric Dimethylbenzo-15-crown-5 Ethers and Some of Their Complexes

With ethyl lactate as an optically active precursor and with employment of Williamson reactions, three isomeric and axially symmetric dimethylbenzo-15-crown-5 ethers were prepared and characterized: (5R,15R)-5,15-dimethyl-5,6,8,9,11,12,14,15-octahydrobenzo-1,4,7,10,13-pentaoxacyclopentadecin and the (6S,14S)-6,14-dimethyl and (8S,12S)-8,12-dimethyl isomers, termed the α, β, and γ isomers, respectively.The circular dichroism spectra of the ethers and their complexes with Na+ in CH3OH have been determined and interpreted in terms of the gross overall orientationof the macrocycle in relation to the aromatic ring.The behavior of the γ-isomer with Ba2+ and with low ratios of K+ suggests dominance of 2:1 (sandwich) complexes.

Alkali Metals Dissolved in Optically Active Solvents

Alkali metals dissolve in amines and ethers to give visible and infrared absorption bands.The visible band is believed to be due to absorption by the alkali metal anion and the infrared band to absorption of light by the solvated electrons.The visible and circular dichroism spectra of sodium-potassium alloy dissolved in several optically active ethers and amines were examined.In all cases, no circular dichroism could be detected corresponding to the alkali anion transition.An excellent synthetic route for the formation of a variety of chiral polyethers and cyclic polyethers is described.The method uses the readily available, chiral ethyl (S)-(+)-lactate.