473759-00-1

Upstream product

• 473758-98-4 Benzoic acid (1R,3S,4S,5S)-6-(4-methoxy-benzyloxy)-1,3,5-trimethyl-2-oxo-4-triethylsilanyloxy-hexyl ester 
• 473758-97-3 (-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 473758-99-5 (2R,4R,5S,6S)-7-(4-Methoxy-benzyloxy)-4,6-dimethyl-5-triethylsilanyloxy-heptane-2,3-diol 

Downstream Products

• 473759-01-2 N-[(Z)-(3R,4R,5S)-6-(4-Methoxy-benzyloxy)-3,5-dimethyl-4-triethylsilanyloxy-hex-1-enyl]-N-methyl-formamide 
• 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 

Relevant academic research and scientific papers

Asymmetric catalysis route to anti,anti stereotriads, illustrated by applications

(Chemical Equation Presented) A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the B-2 intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide cap for the callipeltins.

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.