Synthesis of <i>N</i>δ-Hydroxyornithine

Isowa, Yoshikazu; Takashima, Tsuyoshi; Ohmori, Muneki; Kurita, Hideaki; Sato, Masanari; Mori, Katsuharu

doi:10.1246/bcsj.45.1461

Cited by 24 publications

(8 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…and the recovered auxiliary 1 in high yields (Scheme 2). The w-halide atom in 3m and 3n was also efficiently displaced by 0 -benzyl-N-tosyl-hydroxylamine [23]/KN(SiMe,), or with 0 -benzyl acetohydroxamate [24]/K,CO, in the case of 3n, without apparent N-acyl cleavage or C(a )-epimerization. The resulting o-protected [a -amino-o-(hydroxyamino)acyI]sultams 8m, n (83-93 YO) were subjected to consecutive acidic and basic hydrolysis providing, in addition to recovered sultam 1 (92-93 YO), optically pure N"-(benzy1oxy)-N"-tosyl-substituted ornithine and lysine 13m and 1311, respectively (93-94% ; Entries 5 and 6).…”

Section: Alkylation Of 2 Under Anhydrous Conditions Successive Treatmentioning

confidence: 99%

Asymmetric Alkylations of a Sultam‐Derived Glycine Equivalent: Practical preparation of enantiomerically pure α‐amino acids

Oppolzer

Moretti

Zhou

1994

Helvetica Chimica Acta

105

View full text Add to dashboard Cite

Alkylation of the chiral glycine derivative 2 with 'activated' organohalides under ultrasound-assisted phasetransfer catalysis or with activated and nonactivated organohalides in anhydrous medium provides (mostly crystalline) alkylation products 3. Acidic hydrolysis of the pure products 3 gives (aminoacy1)sultams 4 which by mild saponification furnish pure a -amino acids 5 in good overall yields from 2, along with recovered auxiliary 1 (Scheme I). Pure w-protected a,@-diamino acids and a-amino-w-(hydroxyamin0)acids 12-16 are readily accessible from (w-ha1oacyl)sultams 3 via reaction with N-nucleophiles followed by acidic and basic hydrolyses (Scheme 2). A reliable determination of the enantiomeric purity of a-amino acids using HPLC analysis of their N-(3,5-dinitrobenzoyl)prolyl derivatives 17 is presented.

show abstract

Section: Alkylation Of 2 Under Anhydrous Conditions Successive Treatmentioning

confidence: 99%

Asymmetric Alkylations of a Sultam‐Derived Glycine Equivalent: Practical preparation of enantiomerically pure α‐amino acids

Oppolzer

Moretti

Zhou

1994

Helvetica Chimica Acta

105

View full text Add to dashboard Cite

show abstract

“…Eine 1974 von Isowa et al [4] veroffentlichte Synthese des Ferrichroms ging von der L-Form des 8N-Tosyl-GN-benzyl-oxy-ornithins (5) [5] ,---G l Y .…”

Section: Discussionunclassified

Stoffwechselprodukte von Mikroorganismen. 174. Mitteilung Eine neue Synthese des Ferrichroms; enantio‐Ferrichrom

Naegeli

Keller‐Schierlein

1978

Helvetica Chimica Acta

View full text Add to dashboard Cite

Metabolites of Microorganisms. A New Synthesis of Ferrichrome; enantio‐Ferrichrome The enantiomer of the natural sideramine ferrichrome was synthesized starting from D‐ornithine. The cyclohexapeptide (D‐Orn)3‐Gly3 was obtained by conventional methods of polypeptide chemistry. For the oxidation of the δ‐amino groups of the D‐ornithine residues to hydroxylamino groups the oxaziridine pathway was successful. The final steps ‐ introduction of the acetyl groups and formation of the iron trihydroxamate complex ‐ followed known procedures. The spectroscopic and chromatographic properties of the crystalline product corresponded to those of natural ferrichrome, the optical rotations and CD. curves being opposite. The biological activity of enantio‐ferrichrome was similar to that of the natural sideramine.

show abstract

“…[44][45][46][47] Scheme 9 Synthesis of trans-N-[(2-Phenylcyclopropyl)methyl]hydroxylamine and an N-Propargylhydroxylamine [43,46] Ph OH Variation 3: Alkylation of N-(Benzyloxy)-4-toluenesulfonamide N-(Benzyloxy)-4-toluenesulfonamide (31) is successfully used for the synthesis of various N-hydroxy amino acids. [48][49][50] Similarly, syntheses of N-(2-phosphonoethyl)hydroxylamine (32) and its phosphinopropyl ester analogue 33 can be accomplished in reasonable yields (Scheme 10). [51] Scheme 10 Syntheses of ethyl]phosphonic Acid and propyl]methylphosphinic Acid [51] 72% P(OEt) 3 Addition of hydroxylamine to activated double bonds provides access to polyfunctional Norganohydroxylamines in a simple and straightforward way.…”

mentioning

confidence: 99%