212912-47-5

Upstream product

• 58107-41-8 N-[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]-4-methylbenzenesulfonamide 
• 149-73-5 trimethyl orthoformate 
• 108591-33-9 N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide 

Downstream Products

• 130826-31-2 2-[(4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-1-phenyl-propan-1-one 
• 130826-31-2 (R)-2-[(2R,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-1-phenyl-propan-1-one 
• 129886-59-5 2R,4S,5R,1'R-2-(2'-Oxo-2',5'-dihydroxy-5'-furyl)-4-methyl-3-p-methylphenylsulphonyl-5-phenyl-1,3-oxazolidine 
• 129886-59-5 (R)-5-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-5H-furan-2-one 
• 130826-32-3 2-Methyl-2-[(4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone 
• 130826-32-3 (S)-2-Methyl-2-[(2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone 
• 131142-84-2 (2R,4S,5R)-4-Methyl-2-((R)-1-methyl-allyl)-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidine 
• 131142-85-3 (2S,4S,5R)-4-Methyl-2-((R)-1-methyl-allyl)-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidine 
• 129886-60-8 (S)-2-[(2R,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propan-1-ol 
• 129905-18-6 (R)-2-[(2R,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-pentan-3-one 
• 129886-61-9 (2R,4S,5R)-2-((S)-2-Benzyloxy-1-methyl-ethyl)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidine 
• 131142-87-5 (R)-2-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propan-1-ol 
• 131142-86-4 (R)-2-[(2R,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propan-1-ol 
• 108591-33-9 N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide 

Relevant academic research and scientific papers

NOREPHEDRINE DERIVED 2-METHOXY OXAZOLIDINES AS CHIRAL FORMYL CATION EQUIVALENTS

Lewis acid catalyzed reaction of silylenolethers with 1 followed by a straightforward nondestructive removal of the chiral auxiliary affords the corresponding aldehydes in good e.e.Compound 1 respresents the first effective synthetic equivalent of formyl cation.

Asymmetric synthesis by the use of norephedrine-derived 2-methoxy-oxazolidines. Part four: the synthesis of enantiomerically enriched polyhydroxylated building blocks

The Lewis acid promoted addition of five silylketeneacetals to norephedrine derived 2-methoxy oxazolidines allowed the stereoselective incorporation of an oxy function vicinal to the oxazolidinic C-2 position.Subsequent functional group modification and/or non destructive chirophor removal, afforded enantiomerically enriched polyhydroxylated building blocks such as (S)-di-O-benzyl glyceraldehyde and D-ribose propane-1,3 diyldithioacetal.A rational accounting for the selectivity of the coupling steps is proposed.Keywords: asymmetric synthesis / norephedrine / (S)-di-O-benzylglyceraldehyde / D-ribose propane-1,3-diyldithioacetal