55438-00-1

Upstream product

• 477945-90-7 (2S,3S,6R)-6-(7-Carboxy-heptyl)-3-(dimethyl-phenyl-silanyl)-2-methyl-piperidine-1-carboxylic acid benzyl ester 
• 676565-29-0 (2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester 
• 931405-40-2 methyl (2'R,5'S,6'S)-8-(N-benzyloxycarbonyl-5'-hydroxy-6'-methylpiperidin-2'-yl)octanoate 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 622836-81-1 (5E,7E)-(S)-4-Benzyloxy-11-methoxymethoxy-undeca-5,7-dienoic acid methyl ester 
• 477945-82-7 (S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-14-benzyloxy-3-(dimethyl-phenyl-silanyl)-tetradecane-1,6-dione 
• 477945-86-1 [(1S,2S)-4-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-2-(dimethyl-phenyl-silanyl)-1-methyl-butyl]-carbamic acid benzyl ester 
• 477945-87-2 [(1S,2S)-13-Benzyloxy-2-(dimethyl-phenyl-silanyl)-1-methyl-5-oxo-tridecyl]-carbamic acid benzyl ester 
• 477945-84-9 (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid ethyl ester 
• 477945-83-8 (S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-pentanoic acid ethyl ester 
• 477945-85-0 (2R,3S)-5-[2-(8-Benzyloxy-octyl)-[1,3]dioxolan-2-yl]-3-(dimethyl-phenyl-silanyl)-2-methyl-pentanoic acid amide 
• 477945-89-4 (2S,3S,6R)-3-(Dimethyl-phenyl-silanyl)-6-(8-hydroxy-octyl)-2-methyl-piperidine-1-carboxylic acid benzyl ester 
• 477945-88-3 8-[(2R,5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-methyl-piperidin-2-yl]-octan-1-ol 
• 622836-85-5 benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate 

Downstream Products

• 55534-76-4 dibenzyl (1S,11R,13S,14S,24R,26S)-13,26-dimethyl-3,16-dioxo-2,15-dioxa-12,25-diazatricyclo[22.2.2.2^11,14]triacontane-12,25-dicarboxylate 

Relevant academic research and scientific papers

Synthesis of (+)-carpamic acid from (+)-alanine

(+)-Carpamic acid [(2′R,5′S,6′S)-8-(5′-hydroxy-6′-methylpiperidin-2′-yl)octanoic acid, 1] was synthesized from (S)-alanine, employing intramolecular and reductive amination of acyclic amino ketone 8 as the key step to generate the piperidine ring.

Enantioselective Total Synthesis of (+)-Azimine and (+)-Carpaine

(Matrix presented) The enantioselective total syntheses of (+)-azimine and (+)-carpaine have been developed, starting with (S)-1,2,4-butanetriol as a single source of chirality. The key common feature in these syntheses involves stereoselective intramolecular hetero-Diels-Alder reaction of an acylnitroso compound. The critical macrocyclic dilactonization of the N-Cbz derivatives of azimic acid and carpamic acid was efficiently achieved by using the Yamguchi macrocyclization conditions.

Synthesis of enantiomerically pure all cis-2,3,6-trisubstituted piperidine: A silicon mediated total synthesis of (+)-carpamic acid

A stereoselective total synthesis of (+)-carpamic acid 1 has been achieved from the σ-symmetric 3-[dimethyl(phenyl)silyl]glutaric anhydride 11 featuring its asymmetric desymmetrisation using oxazolidinone 12. The dimethyl(phenyl)silyl group is not only ac