106019-41-4

Upstream product

• 501-53-1 benzyl chloroformate 
• 115947-50-7 (1-aminopentyl)phosphinic acid 
• 115947-49-4 [1-[(diphenylmethyl)amino]pentyl]phosphinic acid 
• 110-62-3 pentanal 

Downstream Products

• 106019-46-9 (1-Benzyloxycarbonylamino-pentyl)-phosphonic acid monobenzyl ester; compound with adamantan-1-ylamine 
• 106019-45-8 benzyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate 
• 1067680-07-2 methyl [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(hydroxy)phosphoryl]acetate 
• 1046116-51-1 methyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphinate 
• 1181104-51-7 methyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate 
• 1067680-11-8 [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(hydroxy)phosphoryl]acetic acid 
• 1261301-07-8 [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(hydroxy)phosphoryl]acetamide 
• 1261301-09-0 O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate 
• 1261301-10-3 methyl [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(methoxy)phosphoryl]acetate 
• 1261301-11-4 [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(methoxy)phosphoryl]acetamide 
• 1261301-13-6 benzyl [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(benzyloxy)phosphoryl]acetate 
• 1261301-14-7 methyl [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(benzyloxy)phosphoryl]acetate 
• 1261301-15-8 tert-butyl [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(benzyloxy)phosphoryl]acetate 
• 1261301-17-0 methyl[((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(adamant-1-yloxy)phosphoryl]acetate 

Relevant academic research and scientific papers

Synthesis of α-carboxyphosphinopeptides derived from norleucine

In the present study, we describe in detail the synthesis of a relatively rare class of phosphorus compounds, α-carboxyphosphinopeptides. We prepared several norleucine-derived α-carboxyphosphinic pseudopeptides of the general formula Nle-Ψ[PO(OH)]-Gly. These compounds could have important applications as transition state-mimicking inhibitors for methionine or leucine aminopeptidases or other enzymes. For the preparation of the key α-carboxyphosphinate protected precursors, we investigated, compared and improved two different synthetic methods described in literature: the Arbuzov reaction of a silylated N-protected phosphinic acid with a bromoacetate ester and the nucleophilic addition of a mixed O-methyl S-phenyl N-protected phosphonic acid or a methyl N-protected phosphonochloridate with tert-butyl lithioacetate. We also prepared two N-Fmoc protected synthons, Fmoc-Nle-Ψ[PO(OH)]-Gly-COOH and Fmoc-Nle-Ψ[PO(OAd)]-Gly-COOH, and demonstrated that these precursors are suitable building blocks for the solid-phase synthesis of α-carboxyphosphinopeptides.

Synthesis of methionine- and norleucine-derived phosphinopeptides

We present herein a straightforward synthesis of N-Fmoc-protected synthons derived from a phosphinic analogue of methionine. These precursors were used successfully for the solid-phase synthesis of methionine-mimic phosphinopeptides using BOP-catalyzed coupling without protection of the phosphoryl moiety. We also prepared a new type of pseudopeptide derived from a phosphinic analogue of norleucine with a -PO(OH)-CH2-COOR moiety.

ORALLY ACTIVE PHOSPHONYL HYDROXYACYL PROLINES

This invention is directed to orally active antihypertensive agents of the formula STR1 wherein R 1 is certain alkyl or aralkyl groups.