127927-62-2

Upstream product

• 100-39-0 benzyl bromide 
• 127927-61-1 (S)-2-dibenzylamino-γ-butyrolactone 

Downstream Products

• 127996-36-5 (3S,4S)-3-Dibenzylamino-pentane-1,4-diol 
• 127927-69-9 (1R,2S)-2-Dibenzylamino-1-phenyl-butane-1,4-diol 
• 127966-41-0 (1S,2S)-2-Dibenzylamino-1-phenyl-butane-1,4-diol 
• 325772-11-0 2-tert-butyldimethylsilyl-5-[(1S,2S)-2-dibenzylamino-1,4-dihydroxybutyl]-N,N-dimethylimidazole-1-sulfonamide 
• 325772-13-2 Dibenzyl-[(2S,3S)-2-(1H-imidazol-4-yl)-tetrahydro-furan-3-yl]-amine 
• 325772-12-1 4⁽⁵⁾-[(1S,2S)-2-dibenzylamino-1,4-dihydroxybutyl]imidazole 
• 325772-14-3 (+)-tert-butyl 4-[(2S,3S)-3-dibenzylaminotetrahydrofuran-2-yl]imidazole-1-carboxylate 
• 325772-17-6 2-tert-butyldimethylsilyl-5-[(2S,3S)-3-dibenzylaminotetrahydrofuran-2-yl]-N,N-dimethylimidazole-1-sulfonamide 

Relevant academic research and scientific papers

Direct stereoselective synthesis of enantiomerically pure anti -β-amino alcohols

Enantiomerically pure anti-β-amino alcohols were synthesized from optically pure α-(N,N-dibenzylamino)benzyl esters, derived from α-amino acids, by the sequential reduction to aldehyde with DIBAL-H at -78 °C and subsequent in situ addition of Grignard reagents. Besides anti-β-amino alcohols, anti-2-amino-1,3-diols and anti-3-amino-1,4-diols were obtained in good yields (60-95%) and excellent stereoselectivity (de > 95%). Our technique is compatible with free hydroxyl groups present in the substrate. To demonstrate the versatility of the method, spisulosine and sphinganine were synthesized in two steps from the appropriate N,N-dibenzyl-l-aminobenzyl ester in 42% and 45% yield, respectively.

Stereoselective synthesis of 4(5)-[(2S,3S)- and (2R, 3R)-3-aminotetrahydrofuran-2-yl)imidazoles using modified and standard mitsunobu cyclizations: Synthetic studies toward novel histamine H3-ligands

4(5)-[(2S,3S)-3-Aminotetrahydrofuran-2-yl)imidazole [(+)-3] and its enantiomer [(-)-(2R,3R)-3] were stereoselectivity synthesized by using both modified and standard Mitsunobu cyclizations from L- and D-methionine, respectively.

TANDEM ALDOLIZATION / LACTONIZATION / DYOTROPIC REARRANGEMENT OF α-AMINO-ALDEHYDES

N,N-dibenzyl-protected α-amino-aldehydes 1 undergo non-chelation-controlled aldol additions of 1-phenoxy-1-trimethylsiloxyethylene 2 followed by β-lactone formation and dyotropic rearrangement, all three reactions being catalyzed by MgCl2.The products, 4-substituted 3-amino-χ-lactones 3, are stereochemically pure (de and ee > 99percent).