80828-13-3

Upstream product

• 120-72-9 indole 
• 1193-68-6 cis-octahydroindole 
• 87623-93-6 (3aR,7aR)-1-(Octahydro-indol-1-yl)-ethanone 
• 4169-27-1 cis-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 87623-95-8 (2S,3aR,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile 
• 87624-03-1 (4aS,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 121795-06-0 (S)-2-{(S)-2-[2-tert-Butoxycarbonylamino-4-(ethoxy-methyl-phosphinoyl)-butyrylamino]-propionylamino}-propionic acid ethyl ester 
• 121795-05-9 2-tert-Butoxycarbonylamino-4-(ethoxy-methyl-phosphinoyl)-butyric acid 2,4,5-trichloro-phenyl ester 
• 121795-10-6 2-t-butoxycarbonylamino-4-(ethoxymethylphosphinoyl)-L-butyric acid 
• 3770-50-1 2-carbethoxyindole 
• 79799-08-9 (2S,3aS,7aS)-Octahydro-indole-2-carboxylic acid ethyl ester 
• 120979-32-0 (S)-2-{(S)-2-[2-Amino-4-(ethoxy-methyl-phosphinoyl)-butyrylamino]-propionylamino}-propionic acid 
• 120979-33-1 N-L-(2-methyl-2-oxo-1,2-azaphospholidin-5-ylcarbonyl)-L-alanyl-L-alanine ethyl ester 

Downstream Products

• 82717-91-7 (+/-)-benzyl (2S,3aS,7aS)-octahydroindole-2-carboxylate p-toluenesulfonic acid salt 
• 1609090-02-9 C₂₀H₂₈NO₉P 
• 1555994-26-7 (2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-29-0 (2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-31-4 (2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-24-5 (1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol 
• 1555994-20-1 (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-22-3 (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 80828-33-7 tert-butyl (2S,3aS,7aS)-1-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)octahydro-1H-indole-2-carboxylate 
• 80828-33-7 (2S,3aS,7aS)-1-[(S)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid tert-butyl ester 
• 80876-04-6 (2R,3aR,7aR)-1-[(S)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid tert-butyl ester 
• 80828-33-7 (2R,3aR,7aR)-1-[(S)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid tert-butyl ester 
• 108449-50-9 (2S,3aS,7aS)-1-[(S)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid 
• 80923-95-1 (2R,3aR,7aR)-1-[(S)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid 

Relevant academic research and scientific papers

Efficient access to N-protected derivatives of (R,R,R)- and (S,S,S)-octahydroindole-2-carboxylic acid by HPLC resolution

The preparation of the proline analogue (2S,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic) and its enantiomer, (2R,3aR,7aR)-Oic, is described. A racemic precursor has been synthesized in good yield and subjected to HPLC resolution on a chiral column. The high efficiency of both the synthetic and chromatographic procedures has allowed the isolation of multigram quantities of each amino acid in enantiomerically pure form and suitably protected for use in peptide synthesis.

Total synthesis and enzyme-substrate interaction of D-, DL-, and L-Phosphinotricine, 'bialaphos' (SF-1293) and its cyclic analogues

DL-Phosphonotricine (3) and its cyclic analogue (4) have been synthesized using the four-component isocyanide condensation of Ugi and Ugi-analogous three-component condensation, respectively. High selectivity of the enzyme-substrate interaction was established with the enzymes α-chymotrypsin, phosphodiesterase I, and alkaline mesintericopeptidase, as well as by separation of the racemic mixture to optical antipodes by the α-chymotripsin. The tripeptide 'bialaphos' (11) and its D-antipode (11a) have been synthesized by the method of activated esters, and the cyclic analogue (15) by the DCC method. It was found that the phospholane L-(5) and the tripeptide (18) exhibit anti-tumour activity.

DIASTEREOSELECTIVE SYNTHESIS OF BICYCLIC AMINO ACIDS VIA RING CONTRACTION OF α-CHLOROLACTAMS

Bicyclic lactams were converted to their α-chloro-derivatives and subjected to ring contraction under basic conditions to give bicyclic acids in diasteroselective fashion.

COUPLING OF β-ACETAMIDO RADICALS WITH α-CHLORO ACRYLONITRILE - A NEW ACCESS TO DISUBSTITUTED PROLINE DERIVATIVES

β-Acetamido radicals are prepared by reduction of organomercurials and coupled with α-chloro-acrylonitrile.The coupling products are further converted to proline derivatives.