60008-23-3

Upstream product

• 15761-38-3 L-N-Boc-Ala 
• 65138-05-8 (S)-2-hydroxy-3-methylbutyric acid benzyl ester 
• 100-44-7 benzyl chloride 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 

Downstream Products

• 178861-41-1 (S)-2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-(4-methoxy-phenyl)-pentanoic acid tert-butyl ester 
• 178861-43-3 (3S,6S,9S,12S)-12-Isopropyl-9-[3-(4-methoxy-phenyl)-propyl]-3-methyl-6-phenylselanylmethyl-1-oxa-4,7,10-triaza-cyclododecane-2,5,8,11-tetraone 
• 178861-39-7 (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-propionyloxy)-3-methyl-butyrylamino]-5-(4-methoxy-phenyl)-pentanoic acid tert-butyl ester 
• 53193-10-5 AM-toxin I 
• 198275-46-6 (3S,6S,9S,12S)-12-Isopropyl-9-[3-(10-methoxy-anthracen-9-yl)-propyl]-3-methyl-6-phenylselanylmethyl-1-oxa-4,7,10-triaza-cyclododecane-2,5,8,11-tetraone 
• 198275-41-1 (S)-2-[(S)-2-((S)-2-Amino-propionyloxy)-3-methyl-butyrylamino]-5-(10-methoxy-anthracen-9-yl)-pentanoic acid benzyl ester 
• 338735-90-3 2-{2-[2-(2-tert-butoxycarbonylamino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-5-[2-nitro-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester 
• 338735-99-2 2-{2-[2-(2-tert-butoxycarbonylamino-3-phenylselanyl-propionylamino)-propionyloxy]-3-methyl-butyrylamino}-4-[2-nitro-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-butyric acid tert-butyl ester 
• 338735-92-5 (3S,6S,9S,12S)-12-Isopropyl-3-methyl-9-{3-[2-nitro-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-propyl}-6-phenylselanylmethyl-1-oxa-4,7,10-triaza-cyclododecane-2,5,8,11-tetraone 
• 338736-01-9 (3S,6S,9S,12S)-12-Isopropyl-3-methyl-9-{2-[2-nitro-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-ethyl}-6-phenylselanylmethyl-1-oxa-4,7,10-triaza-cyclododecane-2,5,8,11-tetraone 
• 338735-97-0 2-[2-(2-tert-butoxycarbonylamino-propionyloxy)-3-methyl-butyrylamino]-4-[2-nitro-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-butyric acid tert-butyl ester 
• 338735-88-9 2-[2-(2-tert-butoxycarbonylamino-propionyloxy)-3-methyl-butyrylamino]-5-[2-nitro-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-pentanoic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of a Fluorescent Analog of Alternariolide (AM-toxin I), a Host-specific Phytotoxin for Apple Leaves

A new fluorescent amino acid, L-2-amino-5-(10-methoxy-9-anthryl)pentanoic acid (L-Amap, 3) was synthesized and incorporated into alternariolide instead of L-Amp (L-2-amino-5-(4-methoxyphenyl)-pentanoic acid).

β-Phenylselenoalanine as a dehydroalanine precursor-efficient synthesis of alternariolide (AM-toxin I)

Alternariolide (AM-toxin) is synthesized in 44% overall yield from L-2-amino-5-(4-methoxyphenyl)pentanoic acid; D-β-phenylselenoalanine is used as the dehydroalanine precursor.

ISOPROPENYL CHLOROCARBONATE (IPCC) IN AMINO ACID AND PEPTIDE CHEMISTRY: ESTERIFICATION OF N-PROTECTED AMINO ACIDS; APPLICATION TO THE SYNTHESIS OF THE DEPSIPEPTIDE VALINOMYCIN

Esterification of N-protected α-amino acids was achieved via isopropenyl chlorocarbonate (IPCC) activation.In situ alcoholysis of the unstable mixed anhydride intermediate was catalised by 4-(dimethylamino)pyridine (DMAP).Competing isopropenyl ester formation was negligible when using methylene chloride as the solvent.A variety of esters from primary and secondary alcohols were obtained with good yields (60 to 90 percent), and even the more hindered tertiobutyl alcohol gave acceptable yields under more drastic conditions.The improvement in depsipeptide synthetic methodology is illustrated by preparation of the antibiotic valinomycin, using IPCC for ester bond formation, and BOP reagent for peptide coupling and the last-step cyclisation.