444789-01-9

Basic information

• Product Name: (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine
• Synonyms: (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine
• CAS NO: 444789-01-9
• Molecular Weight: 452.531
• Mol File: 444789-01-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine(444789-01-9)
• EPA Substance Registry System: (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine(444789-01-9)

Safety Data

• Hazardous Substances Data: 444789-01-9(Hazardous Substances Data)

Upstream product

• 1080-32-6 O,O-diethyl benzylphosphonate 
• 25944-64-3 diethyl (1-phenylethenyl)phosphonate 
• 110117-71-0 (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine 

Downstream Products

• 618894-26-1 ((3S,5S)-2-Ethoxy-2-oxo-3-phenyl-2λ⁵-[1,2]oxaphosphinan-5-yl)-carbamic acid tert-butyl ester 
• 618893-41-7 ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate 
• 618893-58-6 (3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane 
• 444789-52-0 ethyl (2S,4R)-2-amino-4-(diethoxyphosphoryl)-4-phenylbutanoate 

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.

Diastereoselective synthesis of 4-substituted 2-amino-4-phosphonobutanoic acids

Conjugate additions of the lithiated bis-lactim ether derived from cyclo-[Gly-D-Val] 1 to α-substituted vinylphosphonates 2 or electrophilic substitutions on the lithiated bis-lactim ether derived from cyclo-[L-AP4-D-Val] 5 allow direct and stereoselectiv