Dibenzylaminoacetates as useful synthetic equivalents of glycine in the synthesis of α-amino-β-hydroxyacids1

Synthesis and biological evaluation of aziridine-containing analogs of phytosphingosine

“…In order to prevent any coordination of the nitrogen atom of the aziridine ring, we tried to protonate the tertiary amine by adding NH 4 Cl to the reaction mixture as described by Guanti et al for the synthesis of a-amino-b-hydroxyacids. 23 These conditions gave results very close to those obtained with NaBH 4 alone (entry 6). The best results were finally obtained with Me 4 NBH 4 as a reducing agent (entry 7).…”

Synthesis, Structure–Activity, and Structure–Stability Relationships of 2‐Substituted‐N‐(4‐oxo‐3‐oxetanyl) N‐Acylethanolamine Acid Amidase (NAAA) Inhibitors

“…[31] Microwave irradiation of a mixture of dibenzylamine and ethyl chloroacetate gave dibenzylamino ethyl acetate (8), [32] which was acylat- ed with the desired acyl chloride (R 1 = Et, iPr, tBu) to give the corresponding b-keto esters 9 a-c. Acidic chemoselective reduction of the keto functionality with sodium borohydride in the presence of ammonium chloride [31] allowed complete stereoselective synthesis of racemic erythro-b-hydroxyamino esters 10 a-c. After deprotection of the amino functionality by hydrogenation, hydrolysis of the corresponding ester moiety of 14 a-c followed by carbamoylation of the free amino group with activated alcohols 41-44 [28b] (see Supporting Information) led to the desired carbamic acid ester intermediates 15 a-c-16 a-c.…”

Fluorobalhimycin — A New Chapter in Glycopeptide Antibiotic Research.

“…b-Hydroxytyrosine and derivatives were easily obtained as a racemic mixture of four stereoisomers in good yields by using a three-step synthesis. [10] Supplementing a culture of OP696 with 3-fluoro-b-hydroxytyrosine (3-Fht) resulted in antibiotic activity of the culture filtrate against the indicator strain Bacillus subtilis (Figure 1 Figure 2) that corresponds to the molecular mass of 1413.4878 Da and to the elemental composition C 66 H 73 F 2 N 9 O 24 of a twofold fluorinated balhimycin, which we named fluorobalhimycin ( Figure 1).…”