251983-07-0

Upstream product

• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 122-52-1 triethyl phosphite 
• 85-44-9 phthalic anhydride 
• 63-91-2 L-phenylalanine 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 

Downstream Products

• 1583285-57-7 (Z)-diethyl (2-(1,3-dioxoisoindolin-2-yl)-3-phenylallyl)phosphonate 
• 1449520-33-5 C₂₁H₂₂NO₅P 
• 1449519-88-3 (S)-diethyl (1-diazo-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropyl)phosphonate 
• 929901-08-6 (2S)-diethyl 1-cyano-1-trimethylsilyloxy-2-(1,3-dioxoisoindolin-2-yl)-3-phenylphosphonate 
• 150993-49-0 ((1S,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates

The regiospecific and stereoselective 1,2-migration reaction of dialkyl α-diazophosphonates for the synthesis of β-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)4PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to β-amino (E)-enylphosphonates in moderate to good yields.

Trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction: Construction of N,S-acetal quaternary centers

Abstract The trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

Unexpected stereoselective synthesis of (Z)-β-alkenyl substituted β-amino phosphonates through β,γ-dihydrogen shift reaction catalyzed by a copper(I) complex and iodine [Cu(MeCN)4]PF 6/I2

A series of dialkyl a-diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN) 4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl a-diazophosphonates gave a mixture of β,γ-dihydrogen shift and 1,2-hydride migration products and afforded β-alk- enyl-substituted β-amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.

α-Amino acid derived bisphosphonates. Synthesis and anti-resorptive activity

Eleven new bisphosphonates were prepared from naturally-occurring l-amino acids. The synthesis required special attention to amino and side-chain protections. The novel compounds were tested in TPTX (thyroparathyroidectomized) rats against arotinoid-induced hypercalcemia and were compared to alendronate. Most of the compounds showed moderate to no anti-resorptive activity. Two compounds were more active than clodronate, but less than alendronate. Limited SAR conclusions were drawn.

Diastereoselective synthesis of β-amino-α-hydroxy phosphonates via oxazaborolidine catalyzed reduction of β-phthalimido-α-keto phosphonates

Reduction of β-phthalimido-α-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded β-phthalimido-α-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds.