304436-17-7

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 304436-21-3 benzyl (R)-2-allyl-3-oxopiperidine-1-carboxylate 
• 625437-82-3 acetic acid 3-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-6-oxo-piperidin-2-yl ester 
• 625437-81-2 5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1-(4-methoxy-benzyl)-piperidin-2-one 
• 625437-72-1 3-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-piperidine-2,6-dione 
• 625437-84-5 (5S)-6-allyl-5-(tert-butyldimethylsilyloxy)piperidin-2-one 
• 562817-53-2 (3S)-1-(4-methoxybenzyl)-3-hydroxypiperidine-2,6-dione 
• 501-53-1 benzyl chloroformate 
• 244056-97-1 Benzyl 2-allyl-3-oxo-1-piperidinecarboxylate 
• 625437-70-9 (5S,6S)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-piperidin-2-one 

Downstream Products

• 32434-44-9 (+)-isofebrifugine 
• 304436-19-9 benzyl (3aS,7aS)-2-(bromomethyl)-2-methoxyhexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate 
• 304436-20-2 benzyl (3aS,7aS)-2-hydroxy-2-[(4-oxo-3(4H)-quinazolinyl)methyl]hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate 
• 1242338-16-4 (2S,3S)-1-benzyloxycarbonyl-2-((E)-3-(4-chlorophenyl)allyl)-3-hydroxypiperidine 
• 1242338-19-7 (2S,3S)-1-benzyloxycarbonyl-2-((E)-4-(ethoxycarbonyloxy)but-2-enyl)-3-hydroxypiperidine 
• 1242338-20-0 (2S,3S)-1-benzyloxycarbonyl-2-((E)-7-bromohept-2-enyl)-3-hydroxypiperidine 
• 1242338-15-3 (2S,3S)-1-benzyloxycarbonyl-3-hydroxy-2-((E)-4-methoxy-4-oxobut-2-enyl)piperidine 
• 1242338-17-5 (2S,3S)-1-benzyloxycarbonyl-3-hydroxy-2-((E)-4-(trimethylsilyl)but-2-enyl)piperidine 
• 24159-07-7 febrifugine 
• 304436-18-8 benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate 

Relevant academic research and scientific papers

Synthesis of functionalized 3-hydroxypiperidines

The synthetic versatility of three chemoenzymatically prepared hydroxypiperidine building blocks has been explored, resulting in a library of enantiopure functionalized piperidines. Key steps involved N-acyliminium ion-mediated CC-bond formation and cross-metathesis reactions, after which full deprotection led to the set of free 3-hydroxypiperidines.

BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine

The asymmetric BF3·Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based

Asymmetric synthesis of antimalarial alkaloids (+)-febrifugine and (+)-isofebrifugine

Diastereoselective α,-amidoalkylation of N,O-acetal, derivated from controlled regio and diastereoselective reduction of (S)-N-(4-methoxybenzyl)-3-silyloxyglutarimide provided two diastereomeric 6-allyl-5-silyloxy-2-piperidinones in 76:24 selectivity. The transformation of the major diastereomer into a known advanced intermediate allowed the synthesis of (+)-febrifugine and (+)-isofebrifugine.

Asymmetric synthesis of (+)-febrifugine and (+)-isofebrifugine using yeast reduction

The antimalarial agents febrifugine (D-1) and isofebrifugine (D-2) were synthesized from chiral 3-piperidinol (D-4), which was asymmetrically prepared by the yeast reduction of 3-piperidone derivatives (DL-3), with dynamic optical resolution.

Asymmetric synthesis of febrifugine and isofebrifugine using yeast reduction

The antimalarial agents febrifugine ((+)-1) and isofebrifugine ((+)-2) were asymmetrically synthesized from chiral piperidin-3-ol ((+)-4), which was prepared by the reductive dynamic optical resolution of the 3-piperidone derivatives ((±)-3) using baker's