39739-05-4

Basic information

• Product Name: Methyl-(S)-2-phtalimido-4-methylthiobutanoate
• Synonyms: Methyl-(S)-2-phtalimido-4-methylthiobutanoate
• CAS NO: 39739-05-4
• Molecular Formula: C₁₄H₁₅NO₄S
• Molecular Weight: 277.3388
• Mol File: 39739-05-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl-(S)-2-phtalimido-4-methylthiobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-(S)-2-phtalimido-4-methylthiobutanoate(39739-05-4)
• EPA Substance Registry System: Methyl-(S)-2-phtalimido-4-methylthiobutanoate(39739-05-4)

Safety Data

• Hazardous Substances Data: 39739-05-4(Hazardous Substances Data)

Upstream product

• 22509-74-6 N-ethoxycarbonylphthalimide 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 67-56-1 methanol 
• 29588-91-8 (2S)-4-methylthio-2-(1,3-dioxo-2-benzazole-2-yl)butanoic acid 
• 85-44-9 phthalic anhydride 
• 63-68-3 L-methionine 
• 5464-44-8 1,3-dihydro-1,3-dioxo-α(CH2CH2SCH3)-2H-isoindole-2-acetate 

Downstream Products

• 146983-84-8 (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-methanesulfinyl-butyric acid methyl ester 

Relevant articles and documents

Intramolecular carbenoid ylide forming reactions of 2-diazo-3-keto-4- phthalimidocarboxylic esters derived from methionine and cysteine

Methionine, S-benzylcysteine and S-allylcysteine were converted into 2-diazo-3-oxo-4-phthalimidocarboxylic esters 8a-c in three steps. Upon rhodium-catalysed dediazoniation, two intramolecular carbenoid reactions competed, namely the formation of a cyclic sulfonium ylide and that of a six-ring carbonyl ylide. The S-methyl and S-benzyl ylides 12a and b could be isolated, while S-allyl ylide 12c underwent a [2,3]-sigmatropic rearrangement. The short-lived carbonyl ylides derived from methionine and S-benzylcysteine formed head-to-tail dimers by a [3 + 3]-cycloaddition and could be trapped with external dipolarophiles, while the S-allyl derivative 14c yielded the pentacyclic compound 17 by an intramolecular [3 + 2]-cycloaddition reaction.

Photochemical transformations of proteinogenic and non-proteinogenic amino acids

The photochemistry of N-activated enantiomerically pure α-amino acids is described with emphasis on chemo-, regio-, stereo-, and spin selectivity. An especially valuable chromophore is the phthalimido group. The first excited singlet states are short-lived and deactivated (chemically) via homolytic CH cleavage or (physically) via electron-transfer steps. The first excited triplet states are chemically deactivated via electron-transfer reactions and subsequent deprotonation/coupling steps. A wide variety of product types were synthesized, and potential target molecules were available by tuning the reaction conditions. Also remote groups can be activated by means of electron-transfer steps, which represents an attractive new synthetic protocol for macrocyclization.

Photochemistry of N-phthaloyl derivatives of methionine

Photocarboxylation of N-phthaloyl derivatives of methionine sulfoxide 1b and methionine sulfone 1c was observed in acetone as the major reaction. For 1a a fast electron transfer initiated cyclization which leads to the bicyclization product 3 (X-ray structure)was observed in the sensitized photolysis. Direct photolysis of 1a leads preferentially to the tricylic product 4 and the decarboxylation product 5. The methionine methyl ester 6a-c showed electon transfer initiated cyclization (for 6a) and disproportionation (for 6b), whereas 6c proved to be photostable.