119595-99-2

Basic information

• Product Name: (S)-5-Oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester
• Synonyms: (S)-5-Oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester
• CAS NO: 119595-99-2
• Molecular Weight: 425.527
• Mol File: 119595-99-2.mol

Chemical Properties

• CAS DataBase Reference: (S)-5-Oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-Oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester(119595-99-2)
• EPA Substance Registry System: (S)-5-Oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester(119595-99-2)

Safety Data

• Hazardous Substances Data: 119595-99-2(Hazardous Substances Data)

Upstream product

• 119595-73-2 L-α-tert-butyl γ-methyl N-(9-(9-phenylfluorenyl))glutamate 
• 119595-72-1 L-N-(9-(9-phenylfluorenyl))glutamic acid γ-methylester 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 756-79-6 dimethyl methane phosphonate 

Relevant articles and documents

An olefination entry for the synthesis of enantiopure α,ω-diaminodicarboxylates and azabicyclo[X.Y.0]alkane amino acids

A new approach for synthesizing α,ω-diaminodicarboxylates of various chain lengths has opened the way for making a series of azabicyclo[X.Y.0]alkane amino acids of different ring sizes. β-Keto phosphonates 21-23 were synthesized in 71-90% yield by the addition of the lithium anion of dimethyl methyl phosphonate to the ω-methyl ester of α.-tert-butyl N-(PhF)aspartate 3, glutamate 9, and aminoadipate 12 (PhF = 9-phenylfluoren-9-yl). α,ω-Diaminodicarboxylates 24-26 of nine to eleven carbon chain lengths were prepared in 78-87% yield from the Horner-WadsworthEmmons olefination of α-tert-butyl .ZV-(PhF)aspartatc β-aldehyde (5) with aminodicarboxylate-derived β-keto phosphonates 21-23. The power of this approach for making azabicyclo[X.Y.0]alkane amino acid was then illustrated by the first synthesis of enantiopure indolizidin-9-one amino acid 2 in nine steps and >25% overall yield from inexpensive aspartic acid as chiral educt. Hydrogenation of (2S,8S)-di-tcrt-butyl 4-oxo-2,8-bis[N-(PhF)amino]non-4-enedioate (24) in 9:1 EtOH:AcOH furnished a 9:1 diastereomeric mixture of 6-alkylpipecolate 28 that was subsequently transformed into azabicyclo[4.3.0]alkane amino acid 2 via lactam cyclization and protecting group manipulations. Because α,ω-diaminodicarboxylates 25 and 26 may be similarly converted to heterocycles of larger ring sizes and because alkylation of similar ketones can be used to attach side-chains at different points on the heterocycle, this olefination strategy greatly expands our methodology for synthesizing azabicyclo[X.Y.0]alkane amino acids for the exploration of conformation-activity relationships of various biologically active peptides.

Synthesis of enantiopure α,ω-diamino dicarboxylates and azabicycloalkane amino acids by Claisen condensation of α-[N-(phenylfluorenyl)amino] dicarboxylates

Enantiomerically pure (3S,6S,9S)-2-oxo-3-(N-BOC-amino)-1-azabicyclo[4.3.0]nonane-9-carboxyli c acid ((3S,6S,9S)-1) was prepared in 39% overall yield from α-tert-butyl γ-methyl N-(9-(9-phenylfluorenyl))glutamate (5) using a Claisen condensation/reductive amination/lactam cyclization sequence.

Synthesis of 4-Substituted Prolines as Conformationally Constrained Amino Acid Analogues

Anionic substitution of N-(9-(9-phenylfluorenyl))-protected glutamic acid esters proceeds without loss of optical integrity to give 4-substituted glutamic acid derivatives.The 4-methyl, propyl, cyanomethyl, and phenyl analogues have thus been prepared.Pri