219697-75-3

Upstream product

• 220458-72-0 (4S,5S)-3-benzyl-4-formyl-5-vinyl-2-oxazolidinone 
• 91510-85-9 phenyl 2,3;5,6-di-O-isopropylidene-1-thio-α-D-mannofuranoside 
• 220458-74-2 (2S,3R)-5-Benzenesulfonyl-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydro-furan-3-ol 
• 220458-81-1 (3aS,4R,6R,6aS)-4-Benzenesulfonyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 
• 220458-76-4 phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-α-D-lyxofuranosyl sulfone 
• 220458-82-2 phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2,5-dideoxy-5-iodo-α-D-lyxofuranosyl sulfone 
• 220458-75-3 phenyl 2-amino-N-benzyl-2N,3O-carbamoyl-2-deoxy-5,6-O-isopropylidene-α-D-lyxofuranosyl sulfone 

Downstream Products

• 220458-77-5 (4R,5S)-3-benzyl-4-benzyloxymethyl-5-vinyl-2-oxazolidinone 
• 98900-30-2 (2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidinium hydrochloride 
• 220458-80-0 (2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine 
• 220458-78-6 (4R,5S)-3-benzyl-4-benzyloxymethyl-5-(2-hydroxyethyl)-2-oxazolidinone 
• 220458-79-7 (3S,4R)-5-benzyloxy-4--1,3-pentanediol 
• 220458-84-4 Toluene-4-sulfonic acid (3S,4R)-4-(benzyl-tert-butoxycarbonyl-amino)-5-benzyloxy-3-hydroxy-pentyl ester 

Relevant academic research and scientific papers

Synthesis of (2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine from (4S,5S)-3-benzyl-4-formyl-5-vinyl-2-oxazolidinone

(4S,5S)-3-BenzyI-4-formyl-5-vinyl-2-oxazolidinone (2), readily prepared via the reductive elimination of the mannose-derived iodo phenyl sulfone (6b), is used in the synthesis of the alkaloid (2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine (1).

Diastereoselectivity in the addition of organocerium reagents to 4- and 5-oxazolidonecarbaldehydes: Synthesis of syn- and anti-alcohols

Chiral non-racemic 4- and 5-oxazolidonecarbaldehydes, typified by 2 and 7, react highly diastereoselectively with organocerium reagents to give moderate to good yields of syn- and anti-alcohols, respectively. Rationalizations for the observed diastereoselectivites are presented. The synthetic potential of this method is exemplified by the synthesis of C-18-D-ribo-phytosphingosine which was obtained as its tetraacetate.