171189-80-3

Upstream product

• 171189-79-0 (S)-4-Benzyl-3-((2S,3R)-7-benzyloxy-3-hydroxy-2-methyl-heptanoyl)-oxazolidin-2-one 
• 78999-24-3 5-benzyloxy-1-pentanal 

Downstream Products

• 171189-81-4 (2R,3R)-7-Benzyloxy-2-methyl-heptane-1,3-diol 
• 171189-93-8 2,2-Dimethyl-propionic acid (E)-(R)-7-{(S)-4-[(R)-benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-2-oxo-[1,3]dioxolan-4-yl}-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-hept-6-enyl ester 
• 171190-06-0 2,2-Dimethyl-propionic acid (R)-5-benzyloxy-1-((R)-1-methyl-2-phenyl-ethyl)-pentyl ester 
• 171189-82-5 Toluene-4-sulfonic acid (2R,3R)-7-benzyloxy-3-hydroxy-2-methyl-heptyl ester 
• 171189-84-7 2,2-Dimethyl-propionic acid (R)-5-hydroxy-1-((R)-1-methyl-2-phenyl-ethyl)-pentyl ester 
• 171189-83-6 (2R,3R)-7-Benzyloxy-2-methyl-1-phenyl-heptan-3-ol 
• 164215-38-7 2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester 
• 164215-40-1 2,2-Dimethyl-propionic acid (1S,3R,5R,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-oxo-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester 
• 164215-39-8 2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester 
• 164215-33-2 2,2-Dimethyl-propionic acid (1R,8S,9R)-9-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-9-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-8-trimethylsilanyloxy-non-6-ynyl ester 
• 164215-37-6 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester 
• 164215-35-4 2,2-Dimethyl-propionic acid (E)-(1R,8S,9R)-9-benzyloxy-9-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-hydroxymethyl-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-non-6-enyl ester 
• 164215-32-1 2,2-Dimethyl-propionic acid (R)-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-pentyl ester 

Relevant academic research and scientific papers

(+)-Zaragozic acid C: Synthesis and related studies

The asymmetric synthesis of the potent squalene synthase inhibitor (+)-zaragozic acid C is described. The synthesis allows for the preparation of multigram quantities of the dioxabicyclooctane core common to all members of this class of fungal metabolites. Supporting studies include (1) the use of [Cr(OAc)2·H2O]2 for the stereoselective reduction of ynones to trans enones, (2) an investigation of the diastereoselective dihydroxylation of γ-alkoxy-α,β-trans enones, and (3) nucleophilic addition of Me3SiC≡CLi to a dioxabicyclooctanone, wherein the product diastereoselectivity is observed to vary as a function of cosolvents (tertiary amines) and additives (LiBr). In addition, an acylation protocol is reported which permits the regioselective installation of the C(6) O-acyl side chain.