618893-45-1

Basic information

• Product Name: ethyl (2R,3S)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-3-phenylbutanoate
• Synonyms: ethyl (2R,3S)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-3-phenylbutanoate
• CAS NO: 618893-45-1
• Molecular Weight: 443.477
• Mol File: 618893-45-1.mol

Chemical Properties

• CAS DataBase Reference: ethyl (2R,3S)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-3-phenylbutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2R,3S)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-3-phenylbutanoate(618893-45-1)
• EPA Substance Registry System: ethyl (2R,3S)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-3-phenylbutanoate(618893-45-1)

Safety Data

• Hazardous Substances Data: 618893-45-1(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 182207-43-8 ethyl (2R,3S)-2-amino-3-phenyl-4-(diethoxyphosphoryl)butanoate 
• 182207-34-7 (2R,5S,1'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine 
• 100-52-7 benzaldehyde 
• 20408-33-7 diethyl (E)-(2-phenylethenyl)phosphonate 
• 25362-01-0 (Z)-diethyl styrylphosphonate 
• 683-08-9 Diethyl methylphosphonate 

Downstream Products

• 182207-52-9 (2R,4S,5R)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-4-phenyl-2-oxo-1,2-oxaphosphorinane 

Relevant articles and documents

Diastereoselective synthesis of 2-amino-4-phosphonobutanoic acids by conjugate addition of lithiated schoellkopf's bislactim ethers to vinylphosphonates

Conjugate additions of lithiated bislactim ethers derived from cyclo-[Gly-Val] and cyclo-[Ala-Val] to α, β, or α,β -substituted vinylphosphonates allow direct and stereoselective access to a variety of 3- or 4-monosubstituted and 2,3-, 2,4-, or 3,4-disubstituted 2-amino-4-phosphonobutanoic acids (AP4 derivatives) in enantiomerically pure form. The relative stereochemistry was assigned by X-ray diffraction analysis or NMR study of 1,2-oxaphosphorinane derivatives. Competitive eight-membered "compact" and "relaxed" transition-state structures are invoked to rationalize the stereochemical outcome of the conjugate additions.

Conjugate additions of E-alkenylphosphonates to lithiated Schollkopf's bislactim ether: Stereocontrolled access to anti 2-amino-3-substituted-4-phosphonobutanoic acids

Highly face-selective Michael adition of lithiated Schollkopf's bislactim ether (derived from cyclo-[L-val-gly], 7) to E-alkenylphosphonates 2a-d and 1,3-butadienylphosphonate 2e allows a direct and stereocontrolled access to the excitatory amino acid analogues 2,3-anti-2-amino-3-substituted-4-phosphonobutanoic acids 14a-d and 2-amino-6-phosphono-4-hexenoic acid 15. The relative stereochemistry was assigned from a NMR study of cyclic derivatives 16, 17 and 19.