93027-52-2

Upstream product

• 40641-81-4 trans-2,3-epoxy-3-phenylpropan-1-ol 
• 100-46-9 benzylamine 
• 1219933-94-4 (4S,5R)-3-benzyl-5-(hydroxymethyl)-4-phenyloxazolidin-2-one 
• 188200-12-6 Benzyl-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-amine 
• 1134-97-0 2-carbamoyloxymethyl-3-phenyl-oxirane 
• 192764-07-1 N-Benzyl-N-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-hydroxylamine 
• 100-58-3 phenylmagnesium bromide 
• 91190-38-4 N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 

Downstream Products

• 192764-26-4 (1S,2S)-1-Benzylamino-3-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-propan-2-ol 
• 947682-06-6 (-)-(2S,3S,6R)-4-benzyl-2,6-bis(methanesulfonyloxymethyl)-3-phenylmorpholine 
• 947682-07-7 (+)-(1R,2S,5S)-3,7-dibenzyl-2-phenyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane 
• 947682-08-8 (+)-(1R,2S,5S)-3-benzyl-7-methyl-2-phenyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane 
• 947682-10-2 (+)-(1R,2S)-7-methyl-2-phenyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane 
• 1219933-95-5 (1S,2R)-1-(benzylamino)-3-(tert-butyldimethylsilyloxy)-1-phenylpropan-2-ol 
• 223384-33-6 (4R,5S)-3-(benzyl)-(4-methylbenzenesulfonyloxymethyl)-4-phenyloxazolidin-2-one 
• 223384-32-5 3-benzyl-5-hydroxymethyl-4-phenyl-(4S,5S)-1,3-oxazolan-2-one 

Relevant academic research and scientific papers

A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate

An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described. The synthesis relies on a diastereoselective reductive amination, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps.

Enantioselective synthesis of 2-phenyl-9-oxabispidines

A small selection of enantiomerically pure 2-phenyl-9-oxabispidines was synthesized in a three to five step procedure from commercially available starting materials. Ring opening of (R,R)-3-phenylglycidol with benzylamine, condensation with (S)-epichloroh

Indium-mediated facile synthesis of chiral allylic amines

An efficient procedure for the synthesis of chiral allylic amines from 5-iodomethyl-2-oxazolidinones using indium metal in refluxing methanol is described.

Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O- isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2- O-isopropylidene-D-glyceraldehyde. The obtained α,β-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and α- hydroxy-β-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer.

Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

The stereoselective addition of Grignard reagents to α-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols.