104293-55-2

Basic information

• Product Name: Carbamic acid, [(1S)-2-phenyl-1-[(2S,4R)-tetrahydro-4-methyl-5-oxo-2-furanyl]ethyl]-, 1,1-dimethylethyl ester
• CAS NO: 104293-55-2
• Molecular Formula: C18H25NO4
• Molecular Weight: 319.401
• Mol File: 104293-55-2.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S)-2-phenyl-1-[(2S,4R)-tetrahydro-4-methyl-5-oxo-2-furanyl]ethyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S)-2-phenyl-1-[(2S,4R)-tetrahydro-4-methyl-5-oxo-2-furanyl]ethyl]-, 1,1-dimethylethyl ester(104293-55-2)
• EPA Substance Registry System: Carbamic acid, [(1S)-2-phenyl-1-[(2S,4R)-tetrahydro-4-methyl-5-oxo-2-furanyl]ethyl]-, 1,1-dimethylethyl ester(104293-55-2)

Safety Data

• Hazardous Substances Data: 104293-55-2(Hazardous Substances Data)

Upstream product

• 193338-94-2 (5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one 
• 104293-38-1 (4S,5S)-N-methyl-4-hydroxy-5-<<(tert-butyloxy)carbonyl>amino>-6-phenylhex-1-ene-2-carboxamide 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 72155-45-4 Boc-L-phenylalaninal 
• 133333-27-4 tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate 
• 74-88-4 methyl iodide 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 537041-41-1 1,1-dimethylethyl [(1S,2S,4R)-5-(bicyclo[2.2.1]hept-2-ylamino)-2-hydroxy-4-methyl-5-oxo-1-(phenylmethyl)pentyl]carbamate 
• 154160-25-5 (2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-methyl-6-phenyl-hexanoic acid 
• 123482-69-9 (2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid 

Relevant articles and documents

A General Stereocontrolled Synthesis of Hydroxyethylene Dipeptide Isosteres

Hydroxyethylene dipeptide isosteres were synthesized by stereocontrolled hydroboration of homoallylic alcohols derived from syn protected aminoepoxides followed by chemoselective oxidation of the resulting primary alcohols.

Structure-based design: Potent inhibitors of human brain memapsin 2 (β-secretase)

Memapsin 2 (β-secretase) is one of two proteases that cleave the β-amyloid precursor protein (APP) to produce the 40-42 residue amyloid-β peptide (Aβ) in the human brain, a key event in the progression of Alzheimer's disease. On the basis of the X-ray crystal structure of our lead inhibitor (2, OM99-2 with eight residues) bound to memapsin, we have reduced the molecular weight and designed potent memapsin inhibitors. Structure-based design and preliminary structure-activity studies have been presented.

A new synthetic route for the γ-lactone precursors of hydroxyethylene dipeptide isosteres

δ-Phthalimido-γ-ketoesters were obtained by the Pd catalyzed coupling reaction between acid chlorides and organozinc reagents derived from β-iodoesters, and were converted into the γ-lactones precursors of Phe-ψ[H.E.]-Ala and Phe-ψ[H.E.]-Pro (15a,b-18a,b).

HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1' side chain on structure-activity

A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides 1 (L-682,679) and 2 (L-685,434) with various heteroalkyl groups leads to a series of extremely potent inhibitors of the enzyme. Several examples of the most potent inhibitors were very effective in an ex vivo cell based viral spread assay using human H9 T- lymphocytes and the IIIb isolate of HIV-1. Compound 19 is 120 times more potent than 1 and 16 times more potent than 2 in inhibiting the spread of infection in this assay.