135130-98-2

Usage

Uses

Used in Pharmaceutical Industry:
Carbamic acid, [(1S)-2-phenyl-1-[(2R)-tetrahydro-5-oxo-2-furanyl]ethyl]-, 1,1-dimethylethyl ester is used as an intermediate in the synthesis of γ-Secretase Inhibitor. This inhibitor targets the enzyme complex responsible for the cleavage of amyloid precursor protein (APP) to generate amyloid β-peptide (Aβ), which is a major causative agent in Alzheimer's disease (AD). By inhibiting γ-secretase, Carbamic acid, [(1S)-2-phenyl-1-[(2R)-tetrahydro-5-oxo-2-furanyl]ethyl]-, 1,1-dimethylethyl ester can potentially help in the development of treatments for Alzheimer's disease.
Used in Chemical Research:
Due to its unique structure, Carbamic acid, [(1S)-2-phenyl-1-[(2R)-tetrahydro-5-oxo-2-furanyl]ethyl]-, 1,1-dimethylethyl ester can also be used in chemical research for the development of new compounds and materials. Its specific functional groups and structural features make it a valuable starting point for the synthesis of various organic molecules with potential applications in different industries.

Upstream product

• 668436-17-7 tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 72155-45-4 Boc-L-phenylalaninal 
• 145761-24-6 Methanesulfonic acid (R)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl ester 
• 125225-54-9 (4R,5R)-5-hydroxy-6-phenyl-4-hexanolide 
• 178259-04-6 methyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-6-phenyl-(E)-2-hexenoate 
• 160002-06-2 (S)-tert-butyl 3-oxo-1-phenylhex-5-en-2-ylcarbamate 
• 338462-91-2 3-carbethoxy-5(R)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>dihydrofuran-2(3H)-one 
• 134210-25-6 (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 207222-78-4 (S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-hexanoic acid ethyl ester 
• 145285-56-9 (E)-ethyl 6-phenylhex-4-enoate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 98818-40-7 (4R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one 
• 207222-83-1 ((1S,2R)-1-Benzyl-4-butylcarbamoyl-2-hydroxy-butyl)-carbamic acid tert-butyl ester 
• 794525-91-0 (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester 
• 1027947-47-2 (2R,4R,5S)-2-(4-Benzoyl-benzyl)-5-tert-butoxycarbonylamino-4-hydroxy-6-phenyl-hexanoic acid 
• 794525-86-3 tert-butyl (S)-(1-((2R,4R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzyl)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate 
• 1026641-14-4 (2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid 
• 794525-92-1 2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid 
• 794525-87-4 5(S)-tert-butoxycarbonylamino-4(R)-(tert-butyldimethylsilanyloxy)-6-phenyl-2-(4-(2-phenyl-1,3-dioxolan-2-yl)-benzyl)hexanoic acid 
• 794525-90-9 {1S-benzyl-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-2R-hydroxy-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester 
• 794525-89-6 (5-(4-benzoyl-phenyl)-1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-(1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3(1S)-methyl-butylcarbamoyl)-pentyl)carbamic acid tert-butyl ester 
• 794525-88-5 {1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester 
• 794525-93-2 {5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester 
• 98737-42-9 (4R,5R)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one 
• 98818-43-0 (2R,4R,5S)-2-Benzyl-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenylhexanoic acid 

Relevant academic research and scientific papers

A stereocontrolled synthesis of 2R-benzyl-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6- phenyl-hexanoic acid (Phe-Phe hydroxyethylene dipeptide isostere)

2R-Benzyl-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6- phenyl-hexanoic acid, a hydroxyethylene dipeptide isostere corresponding to Phe-Phe, has been synthesized in a practical, stereocontrolled fashion from (L)-phenylalanine.

Stereoselective synthesis of photoreactive peptidomimetic γ-secretase inhibitors

The first asymmetric synthesis of novel, potent photoreactive γ-secretase inhibitors 2 and 3 has been accomplished. Two Stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO2-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing γ-secretase activity in the plasma membrane of intact cells.

Synthesis of a complete series of C-4 fluorinated Phe-Gly mimetics

The complete series of Boc-protected allylic mono- and difluorinated Phe-Gly methyl ester derivatives has been synthesized using facile methods. Diastereomeric allylic alcohol derivatives were used as key intermediates, cis- And trans-aziridine derivative

Asymmetric dihydroxylation route to a dipeptide isostere of a protease inhibitor: Enantioselective synthesis of the core unit of ritonavir

An enantioselective synthesis of the dipeptide isostere of ritonavir has been accomplished utilizing Sharpless asymmetric hydroxylation as the key step.

Peptide inhibitors of aspartic proteinases with hydroxyethylene isostere replacement of peptide bond. I. Preparation of four diastereoisomeric (2R or 2S, 4R or 4S, 5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic acids

By two separate routes were prepared four diastereoisomers of (2R or 2S,5R or 5S)-3-benzyl-5-{(1S)-[(tert-butoxycarbonyl)amino]-2-phenylethyl}tetrahydrofuran- 2-ones (11, 12, 17 and 18). Since the furanones were derived from (S)-phenylalanine, absolute co

Stereocontrolled Addition of Propionate Homoenolate Equivalents to Chiral α-Amino Aldehydes

A highly efficient route is presented for preparation of the medicinally important hydroxyester and lactone intermediates 1 and 2 from chiral α-amino aldehydes via homoenolate methodology.Several reaction variables were found to influence the ratio of che