176504-90-8

Basic information

• Product Name: DIMETHYL ((3S)-4-PHENYL-3-(BOC-AMINO)-2-OXOBUTYL)PHOSPHONATE
• Synonyms: DIMETHYL ((3S)-4-PHENYL-3-(BOC-AMINO)-2-OXOBUTYL)PHOSPHONATE;Dimethyl((3S)-4-phenyl-3-(Boc-amino)-2-oxobutyl)phosphonate≥ 99% (TLC)
• CAS NO: 176504-90-8
• Molecular Formula: C₁₇H₂₆NO₆P
• Molecular Weight: 371.37
• Mol File: 176504-90-8.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DIMETHYL ((3S)-4-PHENYL-3-(BOC-AMINO)-2-OXOBUTYL)PHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL ((3S)-4-PHENYL-3-(BOC-AMINO)-2-OXOBUTYL)PHOSPHONATE(176504-90-8)
• EPA Substance Registry System: DIMETHYL ((3S)-4-PHENYL-3-(BOC-AMINO)-2-OXOBUTYL)PHOSPHONATE(176504-90-8)

Safety Data

• Hazardous Substances Data: 176504-90-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 63-91-2 L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 756-79-6 dimethyl methane phosphonate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 34939-91-8 dimethyl lithiomethylphosphonate 

Downstream Products

• 207222-80-8 (Z)-(S)-2-Benzyl-5-tert-butoxycarbonylamino-4-oxo-6-phenyl-hex-2-enoic acid methyl ester 
• 637024-71-6 ethyl (5S,2Z)-2-methyl-[5-(tert-butoxycarbonyl)amino]-4-oxo-6-phenylhex-2-enoate 
• 1372138-82-3 (E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene 
• 1372138-81-2 (1R,2R,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((R)-pyrrolidin-2-yl)butane-1,2-diol 
• 872033-11-9 (1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol 
• 1372138-76-5 C₅₁H₆₆N₈O₈ 
• 1372138-71-0 C₃₀H₃₄N₂O₆ 
• 1163118-84-0 C₃₂H₃₈N₂O₆ 
• 1372138-72-1 C₃₄H₃₈N₂O₈ 
• 1372138-73-2 C₃₄H₄₂N₂O₆ 
• 872033-09-5 (E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenyloct-4-ene 
• 872033-30-2 C₂₂H₂₈N₂O₄ 
• 872033-12-0 (1S,2S,3S)-3-amino-4-phenyl-1-[(2S)-pyrrolidin-2-yl]butane-1,2-diol 

Relevant articles and documents

Impact of stereochemistry on ligand binding: X-ray crystallographic analysis of an epoxide-based HIV protease inhibitor

A new pseudopeptide epoxide inhibitor, designed for irreversible binding to HIV protease (HIV-PR), has been synthesized and characterized in solution and in the solid state. However, the crystal structure of the complex obtained by inhibitor-enzyme cocrys

Synthesis and biological activity of potent HIV-1 protease inhibitors based on Phe-Pro dihydroxyethylene isosteres

Peptidomimetic inhibitors of HIV-1 PR are still a key resource in the fight against AIDS. Here we describe the synthesis and biological activity of HIV-1 PR inhibitors based on four novel dihydroxyethylene isosteres of the Phe-Pro and Pro-Pro dipeptides. The isosteres, containing four stereogenic centers, were synthesized in high yield and excellent stereoselectivity via the cyclization of epoxy amines derived from α-amino acids. The inhibitors were assembled by coupling the isosteres with suitable flanking groups and were screened against recombinant HIV PR showing activities in the subnanomolar to micromolar range. Two Phe-Pro-based inhibitors active at the nanomolar level were further investigated: both inhibitors combine the ability to suppress HIV-1 replication in infected MT-2 cells with low cytotoxicity against the same cells, thereby displaying a high therapeutic index. These results demonstrate the potential of the new Phe-Pro dihydroxyethylene isostere as a core unit of powerful HIV-1 PR inhibitors.

Angiotensin I-converting enzyme (ace) inhibitors

This invention relates to a process for the synthesis of ketomethylene derivatives of the tripeptide Phe-Gly-Pro (“keto-ACE”, compound 5a) and analogues thereof. The synthesis process proceeds via an α,β-unsaturated keto intermediate. A key feature of the process involves a Horner-Emmons olefination of the, -unsaturated keto-phosphonate with ethyl glyoxylate. Keto-ACE analogues produced by the process of the invention display C-domain selectivity.