83824-81-1

Basic information

• Product Name: (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester
• Synonyms: (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester
• CAS NO: 83824-81-1
• Molecular Weight: 249.266
• Mol File: 83824-81-1.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester(83824-81-1)
• EPA Substance Registry System: (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester(83824-81-1)

Safety Data

• Hazardous Substances Data: 83824-81-1(Hazardous Substances Data)

Upstream product

• 83860-98-4 (2S,3S)-H-3-MeAzy-OMe 
• 74481-56-4 methyl (2S,3S)-N-triphenylmethyl-3-methylaziridine-2-carboxylate 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 52785-41-8 N-benzyloxycarbonyl-O-tert-butylthreonine methyl ester 
• 245115-65-5 (2S)-(benzyloxycarbonylamino)-(3R)-(1,1-dimethylallyloxy)butyric acid methyl ester 
• 887248-84-2 C₁₇H₂₃NO₅ 
• 104543-92-2 C₁₉H₂₇NO₅ 
• 16966-09-9 N-benzyloxycarbonyl-O-t-butyl-L-threonine 
• 245115-66-6 (S)-2-[(2S,3R)-2-Benzyloxycarbonylamino-3-(1,1-dimethyl-allyloxy)-butyrylamino]-3-(1,1-dimethyl-allyloxy)-propionic acid methyl ester 
• 245115-67-7 Cbz-Thr(rprenyl)-Ser(rprenyl)-Ile-OMe 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 83824-90-2 (2S,3R)-2-Benzyloxycarbonylamino-3-cyclohexyloxy-butyric acid methyl ester 
• 83824-89-9 (2S,3R)-2-Benzyloxycarbonylamino-3-sec-butoxy-butyric acid methyl ester 
• 83824-88-8 (2S,3R)-2-Benzyloxycarbonylamino-3-isopropoxy-butyric acid methyl ester 
• 112380-25-3 (2R,3R)-2-Benzyloxycarbonylamino-3-benzylsulfanyl-butyric acid methyl ester 
• 4144-14-3 methyl (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methoxybutanoate 

Relevant articles and documents

Studies on 2-Aziridinecarboxylic Acid. VI. Synthesis of β-Alkoxy-α-Amino Acids via Ring-opening Reaction of Aziridine

The reaction of aziridine derivatives having a urethane-type protecting group with several alcohols in the presence of boron trifluoride etherate afford the corresponding optically pure O-alkylserine and O-alkylthreonine derivatives via a ring-opening reaction of aziridine in good yield.

Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A

The isolation of the cytotoxic Lissoclinum sp. metabolite trunkamide A was reported in 1996. After completion of a total synthesis in 1999, it became clear that the structure of this marine natural product had to be revised. We now report the first preparation of actual trunkamide A in a total synthesis that serves as an unambiguous structural and stereochemical proof. Highlights of our synthetic strategy are a Lewis acid assisted aziridine opening that was used for the preparation of the novel reverse- prenylated serine and threonine side chains as well as an efficient oxazoline-thiazoline interconversion on the macrocyclic skeleton. In addition, several stereoisomers prepared by complementary synthetic protocols serve to illustrate the general scope of our methodology and confirm the configurational assignment.