171189-79-0

Upstream product

• 78999-24-3 5-benzyloxy-1-pentanal 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 

Downstream Products

• 284035-47-8 (2S,3R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanal 
• 284035-45-6 (2R,3R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptan-1-ol 
• 284035-38-7 (2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-carbaldehyde 
• 284035-51-4 Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 284035-53-6 [(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol 
• 284035-52-5 Benzoic acid (2R,4S,5S,6R)-6-(4-benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 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 

Relevant academic research and scientific papers

Synthetic studies on spongistatins: Synthesis of the C29-C44 fragment

A convergent synthesis of the C29-C44 fragment, the common subunit of the spongipyran macrolides is described. The key step of the synthesis is the C-glycosidation reaction which is based on coupling of the lithiated F-ring sulfone with the E-ring aldehyde, and subsequent reductive desulfonylation to afford the E-F bis (pyran) with high stereoselectivity at the anomeric carbon. (C) 2000 Elsevier Science Ltd.

(+)-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.