164215-50-3

Upstream product

• 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 
• 164215-33-2 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 
• 164215-30-9 (R)-4-[(1R,2S)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-trimethylsilanyloxy-but-3-ynyl]-2,2-diethyl-[1,3]dioxolane 
• 164215-28-5 (R)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-2-hydroxy-4-trimethylsilanyl-but-3-ynoic acid ethyl ester 
• 164215-27-4 (R)-3-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-2-ethoxy-5-trimethylsilanyl-pent-1-en-4-yn-3-ol 
• 171189-78-9 (S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-4-trimethylsilanyl-but-3-yne-1,2-diol 
• 164215-29-6 (S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol 
• 164215-42-3 2,2-Dimethyl-propionic acid (1S,3R,4S,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-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester 
• 164215-44-5 Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester 
• 164215-48-9 (1S,3S,4S,5R,6R,7R)-6,7-Diacetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester 
• 164215-46-7 Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester 

Downstream Products

• 156661-55-1 (1S,3S,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(2,2-dimethylpropionyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane 
• 146389-62-0 (+)-zaragozic acid 
• 164215-51-4 (1S,3S,4S,5R,6R,7R)-6,7-Diacetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarboxylic acid di-tert-butyl ester 
• 164215-52-5 (1S,3S,4S,5R,6R,7R)-6,7-Diacetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-4-formyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarboxylic acid di-tert-butyl ester 
• 164215-53-6 tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-6,7-diacetoxy-1-(4-acetoxy-5-methyl-6-phenylhexyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 
• 171190-04-8 tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 
• 171190-05-9 tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,6(4E,6R),7R]-1-(4-acetoxy-5-methyl-6-phenylhexyl)-7-(tert-butoxycarbonyloxy)-4-hydroxy-6-(6-methyl-9-phenyl-4-nonenoyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 
• 156767-39-4 Zaragozic acid C 3,4,5-tris-tert-butyl 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.