83427-81-0

Basic information

• Product Name: 2(3H)-Furanone, dihydro-3-[(triphenylmethyl)amino]-, (S)-
• Synonyms: N-Trityl-L-homoserin-lacton;N-trityl homoserine lactone;N-Trityl-L-homoserine lactone
• CAS NO: 83427-81-0
• Molecular Formula: C23H21NO2
• Molecular Weight: 343.425
• Mol File: 83427-81-0.mol

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, dihydro-3-[(triphenylmethyl)amino]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-3-[(triphenylmethyl)amino]-, (S)-(83427-81-0)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-3-[(triphenylmethyl)amino]-, (S)-(83427-81-0)

Safety Data

• Hazardous Substances Data: 83427-81-0(Hazardous Substances Data)

Usage

Chemical family

Furanone

Derivative

Dihydro derivative of 3-[(triphenylmethyl)amino] furanone

Stereoisomeric configuration

(S)

Known for

Potential biological activities, pharmacological properties, and industrial applications in the synthesis of organic compounds and materials

Upstream product

• 57818-19-6 N-trityl dibenzyl L-aspartate 
• 116393-72-7 dimethyl (2S)-N-(triphenylmethyl)aspartate 
• 116393-73-8 (S)-2-(Trityl-amino)-succinic acid 1-tert-butyl ester 4-methyl ester 
• 102056-89-3 N-Trityl-L-homoserin-phenacylester 
• 57818-19-6 (R)-2-(Trityl-amino)-succinic acid dibenzyl ester 
• 83427-79-6 N-Trityl-L-homoserine 
• 83427-82-1 N-Trityl-S-methyl-methionine sulfonium iodide 
• 80514-68-7 N-trityl-L-methionine 
• 74-88-4 methyl iodide 
• 129049-03-2 (S)-3-(Trityl-amino)-dihydro-furan-2,5-dione 
• 76-83-5 trityl chloride 
• 102056-97-3 N-Trityl-L-homoserin-Triethylammonium-Salz 

Downstream Products

• 2185-03-7 L-homoserine lactone hydrochloride 
• 133038-95-6 (S)-2-(Trityl-amino)-butane-1,4-diol 
• 133038-91-2 cis-N-tritylhomoserine lactol 
• 133038-92-3 trans-N-tritylhomoserine lactol 
• 1617519-63-7 (S)-6-((tert-butyldimethylsilyl)oxy)-N-methoxy-N-methyl-3-oxo-4-(tritylamino)hexanamide 
• 1617519-64-8 (S)-6-((tert-butyldimethylsilyl)oxy)-2-diazo-N-methoxy-N-methyl-3-oxo-4-(tritylamino)hexanamide 
• 1617519-65-9 (2S,3S)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide 
• 1617519-61-5 (2S,3S)-2-(2-hydroxyethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide 
• 1617519-66-0 2-((2S,3S)-3-(methoxy(methyl)carbamoyl)-4-oxo-1-tritylazetidin-2-yl)acetic acid 
• 1617519-67-1 (2S,3S)-2-(2-(benzylamino)-2-oxoethyl)-N-methoxy-N-methyl-4-oxo-1-tritylazetidine-3-carboxamide 
• 1617519-60-4 (1R,5S)-2-benzyl-N-methoxy-N-methyl-3,7-dioxo-6-trityl-2,6-diazabicyclo[3.2.0]heptane-1-carboxamide 
• 1617519-62-6 2-((3S)-2-hydroxy-3-(tritylamino)tetrahydrofuran-2-yl)-N-methoxy-N-methylacetamide 

Relevant articles and documents

Model studies towards the applicability of the readily available (S)-N-tritylaspartic anhydride in the synthesis of amino acids and peptides

Reactions of N-tritylaspartic acid anhydride, readily available through N,N'-dicyclo-hexylcarbodiimide-mediated dehydration of N-tritylaspartic acid, with Grignard and Wittig reagents, bulky hydrides, and amines or alcohols of the benzhydryl type, lead regioselectively to products from attack at the β-carbonyl function.

Application of N-Tritylmethionine in the Preparation of Heterocycles of Biological and Synthetic Interest

Treatment of the methylsulfonium salts of the corresponding N-tritylmethionine derivatives with sodium hydride or potassium tert-butoxide provides the heterocycles N-trityl-L-homoserine lactone (3), (S)- and (R)-3-(N-tritylamino)tetrahydrofuran (7a, 7b), (S)-1-hydroxy-3-(N-tritylamino)-2-pyrrolidinone (14), (S)-4-(N-tritylamino)-1,2-oxazinan-3-one (15), (S)-3-(N-tritylamino)-2-pyrrolidone (23), (S)-1-tert-butyloxycarbonylamino-3-(N-tritylamino)-2-pyrrolidone (27), and (S)-2-methyl-4-(N-tritylamino)-1,2-oxazinan-3-one (18).Methylation of 14 and 15 yields (S)-1-methoxy-3-(N-tritylamino)-2-pyrrolidone (17) and 18, respectively.The stereochemistry of compounds 3, 7a, and 17 has been determined by X-ray crystal structure analysis.

A CONVENIENT NEW SYNTHESIS OF HOMOSERINE LACTONE

N-trityl L-homoserine lactone is synthesised in three steps from L-aspartic acid.

L-Canaline Derivatives of Interest in Peptide Synthesis

(S)-4-(tert-Butyloxycarbonylaminooxy)-2-(tritylamino)butyric acid (8) and the p-toluenesulfonate of phenacyl (S)-2-amino-4-(phthalimidooxy)butyrate (10) have been synthesized from N-tritylhomoserine (2) in five and three steps, respectively.

Synthesis of N-Trityl-L-homoserine

L-Homoserine was tritylated via its silylated product with Me2SiCl2 or Ph2SiCl2 in 65-68percent yield.Also N-Trt-L-methionine upon treatment with MeI and degradation of the resulting sulfonium salt with KOH yielded N-Trt-L-homoserine in 75percent yield.Bo