218914-99-9

Upstream product

• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 104315-07-3 (E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-39-0 benzyl bromide 

Downstream Products

• 250249-04-8 C₅₈H₇₉Br₂ClN₈O₁₁Si 
• 250249-13-9 2-[3-(4-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester 
• 250249-16-2 N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionylamino]-succinamic acid 
• 250249-15-1 N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionylamino]-succinamic acid methyl ester 
• 250249-14-0 N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-hydroxy-phenyl)-propionylamino]-succinamic acid methyl ester 
• 250249-12-8 2-[3-(4-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-hydroxy-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester 
• 250249-10-6 (2R,3R)-ethyl 3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)-3-proxypropanoate 
• 250248-92-1 (4S,5R)-5-(4-Benzyloxy-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 250249-11-7 (2R,3R)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-hydroxy-propionic acid 
• 250248-86-3 (4R,5R)-5-(4-Benzyloxy-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester 
• 250248-88-5 (4S,5R)-5-(4-Benzyloxy-phenyl)-2-oxo-oxazolidine-4-carboxylic acid 
• 218915-01-6 (2R,3R)-2-Amino-3-(4-benzyloxy-phenyl)-3-hydroxy-propionic acid ethyl ester 

Relevant academic research and scientific papers

Enantioselective total syntheses and determination of absolute configuration of marine toxins, oxazinins

The enantioselective total syntheses of natural marine toxins, oxazinin-1, -2, -4, -5, -6 and linear precursor preoxazinin-7 are described. The synthetic highlights include Sharpless asymmetric aminohydroxylation and dihydroxylation, oxa-Michael reaction and intramolecular diastereoselective addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine for the construction of the morpholine ring as key steps. The synthetic route also allowed the synthesis of the epi-preoxazinin and a structurally related secondary metabolite bursatellin isolated in 1980 from sea hare Bursatella leachii pleii and its epimer.

Total synthesis of vancomycin - Part 2: Retrosynthetic analysis, synthesis of amino acid building blocks and strategy evaluations

Retrosynthetic analysis of vancomycin (1) defined vancomycin's aglycon (2) and protected triazene 3 (Figure 1) as advanced intermediates for an eventual total synthesis. Sequential assembly of 3 as shown in Figure 2 (strategy I) and Figure 3 (strategy II) led to amino acid building blocks 8-10 and 12-15, respectively, representing vancomycin's amino acids AA-1 to AA-7. These amino acid fragments were constructed by stereoselective routes and the two synthetic strategies were tested for feasibility. Strategy I, postulating construction of the vancomycin main framework in the order of D-O-E→D-O-E/C-O-D→D-O-E/C-O-D/A-B, suffered from serious epimerization problems at the AA-4 stereocenter; while strategy II, involving the sequence C-O-D→C-O-D/AB→C-O-D/AB/D-O-E proved viable. These findings set the stage for the final drive towards vancomycin's aglycon (2) and vancomycin (1).