Aminomethyl derivatives phosphonic acids

Several acyl derivatives of (aminomethyl)-and (1-aminoethyl)-phosphonic acids, in the latter case including [L-l-([L-alanyl]amino)ethyl]phosphonic acid (alafosfalin), have been prepared in their various diastereoisomeric forms and the... 

In an attempt to obtain diastereoselectivity in the alkylation of derivatives of (aminomethyl)phosphonic acid and so prepare other (1-aminoaikyl)phosphonic acid derivatives in optically active forms, the alkylation (by Mel and PhCH2Br) of the chiral 1,3,2-dioxaphosphorinanes (325 Y=H, CHO C= CHPh or CPh2) as their anions, has been examined. The substrates were derived from 2,4-pentanediol (325 R=H) when the exocyclic P-C bond is oriented equatorialiy preferentially, and from 2-methyl-2,4-pentanediol (325 R=Me) in which the P-C bond prefers the axial position. Unfortunately, in spite of the... 

Many syntheses of (aminoalkyl)phosphonic derivatives have been listed which rely on the participation of phosphorous acid, H3PO3 this, like its diesters, exists in the quinque-valent phosphonic acid structure, (H0)2P(0)H. Such reactions include Mannich-type aminomethylations Similar types of reactions with the involvement of hypophosphorous acid and primary amines lead to (aminomethyl)phosphinic acids (Scheme 54) (R = H), during which the formation of376 (R = H) undoubtedly occurs initially. However, such products cannot be isolated, and views differ as to the relative importance of the subsequent formation of polymers and that of the bis(aminoalkyl)phosphinic acids (377 R = fj 5S4,585 latter type of acid is available through reactions with pre-... 

Several studies have employed Escherichia coli, some strains of which appear to be particularly active in their ability to cause P—C bond fission, and through the use of one of these, a metabolite from ethylphosphonic acid was shown to be a-l-(ethylhydroxyphos-phinoyl)ribose (aminomethyl)phosphonic acid and its 7V-methyl, 7V,A -dimethyl and N-acetyl derivatives are converted into A -methylacetamide, A, A -dimethylacetamide, trimethylamine and 7V-methylacetamide, respectively. ... 

R = H), derived from (+)-oxopinic acid, and (aminomethyl)phosphonic acid diethyl ester, was alkylated in the usual way and the products hydrolysed to give the (S)-( 1-aminoalkyl)phosphonic diesters with 15. 62, 93, and 92% e.e. for R = Me, Et. Bn. and allyl. The reaction between (347 R = Li) and diethyl vinylphosphonate gave the (lS)-(347 R = CH2CH2P02Et2) which was acidolysed ( aqueous acetic acid) to... 

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