116546-79-3

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 116546-78-2 (S)-1-benzyloxy-2-methylpentan-3-one 
• 116652-75-6 (R)-1-(benzyloxy)-2-methylpentan-3-one 
• 116652-76-7 Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid 
• 74924-27-9 methyl (S)-3-benzyloxy-2-methylpropanoate 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 128146-35-0 (2S,3S,4S,5S,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol 
• 128146-35-0 (E)-(2S,3R,4S,5S)-1-Benzyloxy-2,4-dimethyl-oct-6-ene-3,5-diol 
• 160691-47-4 (2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene 
• 156629-02-6 (2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal 
• 156766-84-6 (2R,3S,4R,5S,6S,8S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-9,11-dihydroxy-2,4,6,10,12,13-hexamethyltetradecanolide 
• 156766-85-7 (2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide 
• 156629-06-0 (R)-2-Benzenesulfinyl-3-[(4R,5S,6R)-6-((S)-2-benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-{(2S,4R,5R,6S)-6-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,5-dimethyl-[1,3]dioxan-4-yl}-butan-1-ol 
• 128146-36-1 (4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxane-4-carbaldehyde 
• 128241-47-4 (4S,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxane-4-carbaldehyde 

Relevant academic research and scientific papers

Studies in macrolide synthesis: A stereocontrolled synthesis of oleandolide employing reagent- and substrate-controlled aldol reactions of (S)-1-(benzyloxy)-2-methylpentan-3-one

A highly stereocontrolled total synthesis of oleandolide (2), the aglycon of the macrolide antibiotic oleandomycin (1), has been completed in 8% overall yield (20 steps longest linear sequence, 26 steps in total) with 90% overall diastereoselectivity. Ini

Studies in polypropionate synthesis: High π-face selectivity in syn aldol reactions of tin(II) enolates from (R)-and (S)-1-benzyloxy-2-methylpentan-3-one

Use of Sn(OTf)2/Et3N in the aldol reactions of the α-chiral ethyl ketones (R)- or (S)-1 with aldehydes leads to high stereoselectivity (90-95% ds, >-97% ee) for the 1,2-syn-2,4-syn adduct 7 or ent-7. This substrate-based selectivity is rationalised by chelation of the Sn(II) enolate.

ALDOL REACTIONS IN POLYPROPIONATE SYNTHESIS: HIGH ?-FACE SELECTIVITY OF ENOL BORINATES FROM α-CHIRAL METHYL AND ETHYL KETONES UNDER SUBSTRATE CONTROL.

Use of (c-C6H11)2BCl in the anti-selective aldol reaction of the α-chiral ethylketone 2 leads to high stereoselectivity (>94percent) for the 1,2-anti-2,4-anti isomer 7.The related α-chiral methylketone aldol reaction, 8 9, proceeds with 84-93percent d