218915-03-8

Basic information

• Product Name: (2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid ethyl ester
• Synonyms: (2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid ethyl ester
• CAS NO: 218915-03-8
• Molecular Weight: 542.673
• Mol File: 218915-03-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid ethyl ester(218915-03-8)
• EPA Substance Registry System: (2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid ethyl ester(218915-03-8)

Safety Data

• Hazardous Substances Data: 218915-03-8(Hazardous Substances Data)

Upstream product

• 104315-07-3 (E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate 
• 218914-99-9 (2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate 
• 218915-00-5 (2R,3R)-ethyl-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate 
• 89536-84-5 N-tert-butoxycarbonyl-N-methyl-D-leucine 
• 218915-01-6 (2R,3R)-2-Amino-3-(4-benzyloxy-phenyl)-3-hydroxy-propionic acid ethyl ester 

Downstream Products

• 250249-04-8 C₅₈H₇₉Br₂ClN₈O₁₁Si 
• 218915-06-1 2-[3-(4-benzyloxy-phenyl)-2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester 
• 218915-08-3 N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionylamino]-succinamic acid methyl ester 
• 218915-09-4 N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionylamino]-succinamic acid 
• 218915-07-2 N-[bis-(4-methoxy-phenyl)-methyl]-2-[2-[2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-hydroxy-phenyl)-propionylamino]-succinamic acid methyl ester 
• 218915-05-0 (S)-2-{(2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionylamino}-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester 
• 218915-04-9 (2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid 

Relevant articles and documents

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).