68534-64-5

Upstream product

• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 100-52-7 benzaldehyde 
• 216021-63-5 (1S,2S)-2-benzylideneamino-1-phenyl-1,3-propanediol 
• 157823-75-1 (R)-3-benzyl-4-(hydroxymethyl)oxazolidin-2-one 
• 3173-56-6 benzyl isothiocyanate 
• 591-51-5 phenyllithium 
• 157823-80-8 (S)-3-Benzyl-4-((S)-hydroxy-phenyl-methyl)-oxazolidin-2-one 
• 195144-29-7 (1S,2S)-(+)-2-(benzylideneamino)-1-phenylpropane-1,3-diol 
• 867344-14-7 (S)-3-Benzyl-2-oxo-oxazolidine-4-carboxylic acid 
• 157823-78-4 (S)-4-Benzoyl-3-benzyl-oxazolidin-2-one 
• 157823-76-2 (4S)-3-benzyl-2-oxo-oxazolidine-4-carboxylic acid methyl ester 

Downstream Products

• 221048-57-3 (1S,2S)-(+)-2--1-phenylpropane-1,3-diol 
• 221048-55-1 (1S,2S)-(+)-2-(N-allyl-N-benzylamino)-1-phenylpropane-1,3-diol 
• 155595-12-3 (1S,2S)-2-(dibenzylamino)-1-phenylpropane-1,3-diol 

Relevant academic research and scientific papers

Stereoselective synthesis of 3-mono- and 1,3-disubstituted 4-phenyl- 1,2,3,4-tetrahydroisoquinolines

(1S,2S)-(+)-Thiomicamine was transformed in high yield and with high diastereoselectivity into (3R,4R)-4-phenyl-1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid and enantiomerically pure (3R,4R)-3-hydroxymethyl-4-phenyl- and (1R,3R,4R)-3-hydroxymethyl-1-

Formation of enantiopure β-amino alcohols with a 3-oxa-2,7- diazabicyclo[3.3.0]octane framework

N-Allylamino alcohols 11a-g were prepared from enantiopure (1S, 2S)-2- amino-1-phenylpropane-1,3-diol (8) by various reaction pathways. Selective Swern oxidation of the primary alcohol group of compounds 11 followed by treatment of the resulting aldehyde with N-alkylhydroxylamines afforded the corresponding nitrones that underwent an intramolecular 1,3-dipolar cycloaddition to give the bicyclic compounds 12 and 13. 12c and 13c (R3 = allyl) were deallylated providing compounds 12i and 13i, which could be methylated subsequently yielding 12k and 13k, respectively. X-ray analyses of 13a,c and 12g were performed indicating different conformations of 13a and c on the one hand and of 12g on the other hand. Conclusions concerning the conformation of the other compounds 12 and 13 were drawn from their 1H NMR data. Compounds 12 and 13 act as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde, however, the enantiomeric excess of the 1-phenylpropane-1-ol is usually low, the best result (79% ee) was achieved with compound 12c.

Enantioselective catalysis, 109 [1] new expanded chiral bipyridines

Optically active two and three layer nitrogen ligands were synthesized by reacting the N-BOC-protected aminoalcohols (1S,2S)-2-amino-1-phenyl-1,3-propanediol and (S)-2-amino-1,4-butanediol with chloromethyl-benzoic acid chlorides. Expansion was carried out at the chloromethyl substituents via nucleophilic substitution with N-methylated (R)-1-phenylethylamine. The deprotected substances were N-benzylated and reacted with 6,6′-bis(bromomethyl)-2,2′-bipyridine to give the new optically active expanded bipyridine ligands.

Reaction of (1S,2S)-2-amino-1-phenyl-1,3-propanediol with thioacids under the Mitsunobu reaction condition

The Mitsunobu thioesterification was applied to the title 2-amino-1,3-propanediol (1). The regio- and stereochemistry of the reaction was investigated in correlation with the nature of substituents attached to the nitrogen.

Diastereoselective Synthesis of γ-Hydroxy-β-amino Alcohols, (2S,3S)- and (2S,3R)-Threoninol and -Hydroxyphenylalaninol, from (R)-Glycidol via the Derived 4-Hydroxymethyloxazolidinone

Syntheses of enantiomerically pure (2S,3S)- and (2S,3R)-threoninol and (2S,3R)-hydroxyphenylalaninol are demonstrated starting from (R)-glycidol via (S)-4-methoxycarbonyl-2-oxazolidinone by monoalkylation of the ester followed by diastereoselective reduct