128019-40-9

Upstream product

• 143978-60-3 (3S,4aS,8aS)-3-tert-Butylcarbamoyl-octahydro-isoquinoline-2-carboxylic acid tert-butyl ester 
• 75-64-9 tert-butylamine 
• 149182-72-9 (S)-N-tert-butyl-1,2,3,4-tetrahydro-3-isoquinoline-carboxamide 
• 74163-81-8 L-Tic-OH 
• 149182-71-8 benzyl 3(S)-(t-butylcarbamoyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate 
• 115238-59-0 (4aS,8aS)-N-Boc-decahydroisoquinolin-3(S)-carboxylic acid 
• 1064005-84-0 (S)-1,2,3,4-Tetrahydro-isoquinoline-3-carbonyl chloride 
• 79261-58-8 (S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester 
• 63-91-2 L-phenylalanine 
• 149510-69-0 (3S,4aS,8aS)-Decahydro-isoquinoline-3-carboxylic acid methyl ester 

Downstream Products

• 142580-65-2 [(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester 
• 136465-90-2 N-tert-butyl-2-<2(R)-hydroxy-4-phenyl-3(S)-azidobutyl>decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 137431-05-1 2-<3(S)-(Benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136465-78-6 N-tert-Butyldecahydro-2-(2(R)-hydroxy-4-phenyl-3(S)phthalimidobutyl)-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 150323-18-5 (3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 
• 188936-07-4 (3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide 
• 159991-24-9 [(1S,2R)-3-((3S,4aS,8aS)-3-tert-Butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-1-phenylsulfanylmethyl-propyl]-carbamic acid benzyl ester 
• 159878-04-3 (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide 
• 201402-97-3 2-{(S)-4-[(R)-2-((3S,4aS,8aS)-3-tert-Butylcarbamoyl-octahydro-isoquinolin-2-yl)-1-hydroxy-ethyl]-4,5-dihydro-oxazol-2-yl}-benzoic acid methyl ester 
• 159989-64-7 nelfinavir 
• 870073-16-8 C₂₉H₄₂⁽²⁾H₅N₃O₄ 
• 870073-17-9 2-(3-amino-2-hydoxy-4-[2H₅]phenyl-butyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 
• 737767-64-5 (-)-(3S,4aS,8aS,2'R,3'R)-2-[3'-amino-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide 
• 737767-63-4 (3S,4aS,8aS)-2-((4R,5R)-4-Benzyl-2-oxo-oxazolidin-5-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 

Relevant academic research and scientific papers

Asymmetric synthesis of optically active decahydroisoquinolines useful in HIV-1 protease inhibitor synthesis

An efficient synthesis of amino acid ester 8 is described featuring an asymmetric aza-Diels-Alder reaction of diene 5 and chiral imine 6 which establishes the asymmetry at C-3. Hydrogenation of 7 provides 8 with the desired asymmetry at C-4a and C-8a.

Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research

The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.

Towards the synthesis of HIV-protease inhibitors. Synthesis optically pure 3-carboxyl-decahydroisoquinolines

The synthesis of optically pure decahydroisoquinoline 1, a component of HIV-protease inhibitors, was accomplished in 30-33% overall yield from the readily available optically pure monoacid 4.

A Series of Potent HIV-1 Protease Inhibitors Containing a Hydroxyethyl Secondary Amine Transition State Isostere: Synthesis, Enzyme Inhibition, and Antiviral Activity

A series of HIV-1 protease inhibitors containing a novel hydroxyethyl secondary amine transition state isostere has been synthesized.The compounds exhibit a strong preference for the (R) stereochemistry at the transition state hydroxyl group.Molecular modeling studies with the prototype compound 11 have provided important insights into the structural requirements for good inhibitor-active site binding interaction.N-Terminal extension of 11 into the P2-P3 region led to the discovery of 19, the most potent enzyme inhibitor in the series (IC50 = 5.4 nM). 19 was shown to have potent antiviral activity in cultured MT-4 human T-lymphoid cells.Comparison of analogs of 19 with analogs of 1 (Ro31-8959) demonstrates that considerably different structure-activity relationships exist between these two subclasses of hydroxyethylamine HIV-protease inhibitors.