2‐Oxocephems. II. ‐ synthesis of 2‐oxocephalexin from hetacillin

Ernest, I.

doi:10.1002/hlca.19800630119

Cited by 14 publications

References 5 publications

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tert‐Butoxycarbonylation of Amino Acids and their Derivatives:N‐tert‐Butoxycarbonyl‐l‐phenylalanine

Keller¹,

Keller²,

Look³

et al. 2003

Organic Syntheses

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tert ‐Butoxycarbonylation of amino acids and their derivatives: N‐tert ‐butoxycarbonyl‐l‐phenylalanine reactant: 223 g (1 mol) of di‐tert‐butyl dicarbonate product: N‐tert‐butoxycarbonyl‐L‐phenylalanine product: Boc‐Ala‐OH product: Boc‐β‐Ala‐OH product: Boc‐Arg‐OH product: Boc‐Arg(NO2)‐OH product: Boc‐Asn‐OH product: Boc‐Asp(OBzl)‐OH product: Boc‐Cys(Bzl)‐OH product: (Boc‐Cys‐OH)2 product: Boc‐Gln‐OH product: Boc‐Glu(OBzl)‐OH product: Boc‐Gly‐OH product: Boc‐His(Boc)‐OH product: Boc‐Ile‐OH product: Boc‐Leu‐OH product: Boc‐Lys(Boc)‐OH product: Boc‐Lys(CBZ)‐OH product: Boc‐Met‐OH product: Boc‐Met‐OH product: Boc‐Pro‐OH product: Boc‐Ser‐OH product: Boc‐Ser(Bzl)‐OH product: Boc‐Thr‐OH product: Boc‐Trp‐OH product: Boc‐Trp‐(FOR)‐OH product: Boc‐Tyr‐OH product: Boc‐Tyr‐OH product: Boc‐Tyr(Bzl)‐OH product: Boc‐Tyr(2,6‐Cl2‐Bzl)‐OH product: Boc‐Val‐OH

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tert‐Butoxycarbonylation of Amino Acids and their Derivatives:N‐tert‐Butoxycarbonyl‐l‐phenylalanine

Keller¹,

Keller²,

Look³

et al. 2003

Organic Syntheses

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Synthesis and Chemistry of α,β‐Didehydroamino Acids

Kazmaier¹

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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α‐Unsaturated 3‐Amino‐1‐carboxymethyl‐β‐lactams as Bacterial PBP Inhibitors: Synthesis and Biochemical Assessment

Decuyper

Magdalenić

Verstraete

et al. 2019

Chemistry A European J

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Innovative monocyclic β‐lactam entities create opportunities in the battle against resistant bacteria because of their PBP acylation potential, intrinsically high β‐lactamase stability and compact scaffold. α‐Benzylidene‐substituted 3‐amino‐1‐carboxymethyl‐β‐lactams were recently shown to be potent PBP inhibitors and constitute eligible anchor points for synthetic elaboration of the chemical space around the central β‐lactam ring. The present study discloses a 12‐step synthesis of ten α‐arylmethylidenecarboxylates using a microwave‐assisted Wittig olefination as the crucial reaction step. The library was designed aiming at enhanced β‐lactam electrophilicity and extended electron flow after enzymatic attack. Additionally, increased β‐lactamase stability and intermolecular target interaction were envisioned by tackling both the substitution pattern of the aromatic ring and the β‐lactam C4‐position. The significance of α‐unsaturation was validated and the R39/PBP3 inhibitory potency shown to be augmented the most through decoration of the aromatic ring with electron‐withdrawing groups. Furthermore, ring cleavage by representative β‐lactamases was ruled out, providing new insights in the SAR landscape of monocyclic β‐lactams as eligible PBP or β‐lactamase inhibitors.

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2‐Oxocephems. II. ‐ synthesis of 2‐oxocephalexin from hetacillin

Cited by 14 publications

References 5 publications

tert‐Butoxycarbonylation of Amino Acids and their Derivatives:N‐tert‐Butoxycarbonyl‐l‐phenylalanine

tert‐Butoxycarbonylation of Amino Acids and their Derivatives:N‐tert‐Butoxycarbonyl‐l‐phenylalanine

Synthesis and Chemistry of α,β‐Didehydroamino Acids

α‐Unsaturated 3‐Amino‐1‐carboxymethyl‐β‐lactams as Bacterial PBP Inhibitors: Synthesis and Biochemical Assessment

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