592531-07-2

Upstream product

• 33375-06-3 (1R)-1-phenylethyl isocyanate 
• 57044-25-4 (R)-oxiranemethanol 
• 60456-23-7 (S)-oxiranemethanol 
• 252351-21-6 (4S)-4-hydroxymethyl-N-[(αR)-α-methylbenzyl]-2-oxazolidinone 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 74124-79-1 di(succinimido) carbonate 
• 252351-20-5 (R)-2-[(α-methylbenzyl)amino]-1,3-propanediol 
• 609826-46-2 (2S,αR)-3-hydroxy-2-[(α-methylbenzyl)amino]propyl 4-nitrobenzoate 
• 592531-06-1 diethyl (R)-(α-methylbenzyl)aminomalonate 
• 627-11-2 2-Chloroethyl chloroformate 
• 609826-53-1 (4R,αR)-(3-α-methylbenzyl-2-oxazolidinon-4-yl)methyl 4-nitrobenzoate 
• 252351-23-8 2-chloroethyl 3-hydroxy-2-[(αR)-α-methylbenzyl]aminopropyl carbonate 

Downstream Products

• 252351-21-6 (4S)-4-hydroxymethyl-N-[(αR)-α-methylbenzyl]-2-oxazolidinone 
• 1353577-14-6 (4R,αR)-4-(hexadecyloxymethyl)-3-(α-methylbenzyl)oxazolidin-2-one 

Relevant academic research and scientific papers

Studies on two different diastereoselective reaction pathways from a serinol derivative to 4-hydroxymethyl-2-oxazolidinones using 2-chloroethyl chloroformate and N,N′-disuccinimidyl carbonate

Two reaction pathways and their diastereoselectivity-determining steps of the asymmetric desymmetrization of (R)-2-(α-methylbenzyl)amino-1,3- propanediol 1 with 2-chloroethyl chloroformate (CCF) and with N,N′-disuccinimidyl carbonate giving (4S,αR)-4-hydr

Diastereoselective intramolecular acyl transfer of 5-(α-methylbenzyl)amino-1,3-dioxan-2-one to 4-hydroxymethyl-2-oxazolidinones

Intramolecular acyl transfer of (R)-5-(α-methylbenzyl)amino-1,3-dioxan-2-one (2) by treatment with DBU in CD2Cl2, CDCl3, C6D6, CD3CN, CD3NO2, DMSO-d6, DMF,

One-pot acylation and fractional crystallization: Preparation of optically active serinol monobenzoates

Mono-O-acylation of (R)-2-(α-methylbenzyl)amino-1,3-propanediol 1 with 4-nitrobenzoyl chloride and DMAP in dichloromethane at room temperature gave crystals of optically active (2S,αR)-3-hydroxy-2-(α-methylbenzyl)aminopropyl 4-nitrobenzoate hydrochloride

A novel dynamic kinetic resolution accompanied by intramolecular transesterification: Asymmetric synthesis of a 4-hydroxymethyl-2-oxazolidinone from serinol derivatives

Reaction paths of the one-pot reaction of (R)-2-(α-methylbenzyl)amino-1,3-propanediol (1) and 2-chloroethyl chloroformate with DBU giving (4S,αR)-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone [(4S)-2] (94% de) were investigated. Intermediates of this reaction, 2-chloroethyl (2S)- and 2-chloroethyl (2R)-3-hydroxy-2-[(αR)-α-methylbenzyl]aminopropyl carbonates [(2S)-4 and (2R)-4], were synthesized individually. After the addition of DBU to the respective solution of the carbonate (2S)-4 and that of (2R)-4 in dichloromethane, the intramolecular transesterification between (2S)-4 and (2R)-4 and the diastereoselective intramolecular cyclization proceeded to afford (4S)-2 in high diastereomeric excess. Therefore, two monocarbonates (2S)-4 and (2R)-4 were kinetically resolved by this cyclization during the intramolecular transesterification between (2S)-4 and (2R)-4. We found that this process involved dynamic kinetic resolution accompanied by intramolecular transesterification.

Asymmetric synthesis of the 4-hydroxymethyl-2-oxazolidinone from the serinol derivative and chloroformates

Asymmetric desymmetrization of 2-[(αR)-α-methylbenzyl]amino-1,3-propanediol (1) with 2-chloroethyl chloroformate and DBU at room temperature gave optically active (4S)-4-hydroxymethyl-N-[(αR)-α-methylbenzyl]-2-oxazolidinone [(4S)-2] (up to 94% de). This r