290354-73-3

Upstream product

• 139877-36-4 (3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 290354-67-5 Methyl (2R)-3-(tert-butyldiphenylsiloxy)-2-(dibenzylamino)propanoate 
• 290354-68-6 (2S)-3-tert-butyldiphenylsilyloxy-2-(N,N-dibenzylamino)propan-1-ol 
• 627859-97-6 (R)-4-Benzyl-3-[(2S,3R,4R)-2-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-4-dibenzylamino-3-hydroxy-pentanoyl]-oxazolidin-2-one 
• 627859-92-1 (2S,3R,4R)-2-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-4-dibenzylamino-3-hydroxy-pentanoic acid methyl ester 
• 290354-71-1 (2'S,3'R,4S,4'R)-4-Benzyl-3-[2'-benzyloxy-5'-(tert-butyldiphenylsiloxy)-4'-dibenzylamino-3'-hydroxypentanoyl]oxazolidin-2-one 
• 290354-66-4 (2S)-3-(tert-Butyldiphenylsiloxy)-2-(dibenzylamino)propanal 
• 290354-72-2 (2S,3R,4R)-2-Benzyloxy-5-(tert-butyldiphenylsiloxy)-4-dibenzylamino-3-hydroxy-N-methoxy-N-methylpentanamide 

Downstream Products

• 200282-97-9 (2R,3R,4R)-2-(tert-Butyldiphenylsiloxymethyl)-3,4-dihydroxypyrrolidine 

Relevant academic research and scientific papers

Enantioselective Formal Synthesis of Nectrisine Using a Palladium-Catalyzed Asymmetric Allylic Amination and Cross-Metathesis as Key Steps

A formal enantioselective synthesis of nectrisine, a potent α-glucosidase inhibitor, was carried out starting from butadiene monoepoxide through a synthetic sequence involving enantioselective allylic substitution, cross-metathesis, dihydroxylation, and cyclization.

Short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B and a formal synthesis of nectrisine

(Chemical Equation Presented) A short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B is reported. Garner's (R)-aldehyde, prepared from D-serine, was the chiral starting material. The pyrrolidine ring was stereoselectively created in a very efficient way through a five-step, one-pot transformation. In addition, an intermediate of this synthesis was transformed into an intermediate of a previously published synthesis of the potent α-glucosidase inhibitor nectrisine.

Stereoselective synthesis of the α-glucosidase inhibitor nectrisine

The α-glucosidase inhibitor nectrisine was synthesised in 12 steps (31% overall yield) starting from D-serine. The three contiguous stereocentres of this iminosugar were introduced via a highly diastereoselective boron mediated glycolate aldol reaction.

A flexible and efficient synthesis of the pyrrolidine α-glycosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol (DAB-1)

The synthesis of the pyrrolidine α-glycosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol (DAB-1) was discussed. The synthesis used serine-derived α-dibenzylamino aldehyde in a highly diastereoselective glycolate aldol reaction. The glycolate derivative of Evans' oxazolidinone compound was found to be prepared using benzyl-oxyacetyl chloride and 4-benzyloxazolidin-2-one. The analysis showed that the deprotection of the N-benzyl protecting groups was completed within the first 2-3 h of the reaction.