473758-97-3

Upstream product

• 132969-60-9 (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal 
• 460997-47-1 (-)-(R)-3-oxopentan-2-yl benzoate 
• 136320-64-4 (2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol 
• 93-97-0 benzoic acid anhydride 
• 132969-71-2 methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate 
• 473758-96-2 C₆H₅CO₂CH(CH₃)C(C₂H₄)OB(C₆H₁₁)2 

Downstream Products

• 473759-09-0 Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-2,4,8,10-tetramethyl-7-oxo-3,9-bis-triethylsilanyloxy-dodeca-5,11-dienyl ester 
• 473759-11-4 Isobutyric acid (Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodec-11-enyl ester 
• 473759-10-3 Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodeca-5,11-dienyl ester 
• 473759-08-9 Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester 
• 473758-99-5 (2R,4R,5S,6S)-7-(4-Methoxy-benzyloxy)-4,6-dimethyl-5-triethylsilanyloxy-heptane-2,3-diol 
• 473759-01-2 N-[(Z)-(3R,4R,5S)-6-(4-Methoxy-benzyloxy)-3,5-dimethyl-4-triethylsilanyloxy-hex-1-enyl]-N-methyl-formamide 
• 473759-00-1 (2S,3S,4S)-5-(4-methoxybenzyloxy)-2,4-dimethyl-3-(triethylsilyloxy)pentanal 
• 473758-98-4 Benzoic acid (1R,3S,4S,5S)-6-(4-methoxy-benzyloxy)-1,3,5-trimethyl-2-oxo-4-triethylsilanyloxy-hexyl ester 

Relevant academic research and scientific papers

Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers

A total synthesis of the proposed structure of nhatrangin A is described. This strategy relies on two aldol reactions to install the chiral centers at C3/C4 and C3′/C4′, a lithium-mediated coupling between an advanced intermediate alkyne and a Weinreb amide to complete the C1-C13 alkyl scaffold, and a Yamaguchi esterification to set the side chain. Discrepancies in the spectroscopic data between synthetic and natural nhatrangins led us to synthesize six more diastereoisomers of the proposed structure of nhatrangin A.

Studies in marine macrolide synthesis: Stereocontrolled synthesis of a C21-C34 subunit of the aplyronines

The C21-C34 subunit 27 of the aplyronines, containing eight stereocentres and a terminal N-methyl-N-vinylformamide moiety, was prepared using the Horner-Wadsworth-Emmons coupling of β-ketophosphonate 5 with aldehyde 19. The two stereotetrad sequences were constructed by chiral ketone aldol reactions, while the N-methyl-N-vinylformamide was introduced using a novel Wittig olefination.