164215-33-2

Upstream product

• 25636-49-1 3,3-dimethoxypentane 
• 78999-24-3 5-benzyloxy-1-pentanal 
• 164215-25-2 (R)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-hydroxy-N,N-dimethyl-acetamide 
• 164215-32-1 2,2-Dimethyl-propionic acid (R)-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-pentyl ester 
• 164215-26-3 (R)-2-Benzyloxy-2-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-N,N-dimethyl-acetamide 
• 164215-29-6 (S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol 
• 171189-77-8 (R)-1-Benzyloxy-1-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-ethoxy-but-3-en-2-one 
• 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 
• 164215-27-4 (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 
• 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 
• 171189-79-0 (S)-4-Benzyl-3-((2S,3R)-7-benzyloxy-3-hydroxy-2-methyl-heptanoyl)-oxazolidin-2-one 
• 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 

Downstream Products

• 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 
• 164215-53-6 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 
• 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 
• 164215-44-5 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 
• 164215-51-4 (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 
• 164215-48-9 (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 
• 164215-50-3 (1S,3S,4S,5R,6R,7R)-6,7-Diacetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-formyl-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 
• 164215-47-8 Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester 
• 164215-45-6 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-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester 
• 164215-49-0 (1S,3S,4S,5R,6R,7R)-6,7-Diacetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-4-hydroxy-5-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester 
• 164215-43-4 (1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol 
• 156767-39-4 Zaragozic acid C 3,4,5-tris-tert-butyl ester 
• 146389-62-0 (+)-zaragozic acid 

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.