154491-89-1

Upstream product

• 147963-63-1 ethyl (R)-3-(tert-butyldiphenylsilyloxy)butyrate 
• 1206620-80-5 tert-butyl-[(R)-3-(4-methoxy-benzyloxy)-1-methylpropoxy]-diphenyl-silane 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 154491-90-4 (R)-3-((tert-butyldiphenylsilyl)oxy)-1-iodobutane 
• 183310-90-9 (R)-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde 
• 1403608-12-7 5-{[(3R)-3-{[tert-butyl(diphenyl)silyl]oxy}butyl]sulfonyl}-1-phenyl-1H-tetrazole 
• 1403608-18-3 (4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane 
• 154491-91-5 (R)-methyl 7-((tert-butyldiphenylsilyl)oxy)-3-oxooctanoate 
• 878627-90-8 5-[3-(tert-butyl-diphenyl-silanyloxy)-butyl]-5-methoxy-5H-furan-2-one 
• 878627-89-5 tert-butyl-(3-furan-2-yl-1-methyl-propoxy)-diphenyl-silane 

Relevant academic research and scientific papers

Mild deprotection of PMB ethers using tert-butyl bromide

A convenient and high yielding method for the cleavage and scavenging of p-methoxybenzyl protecting group of several alcohols using tert-butyl bromide in refluxing acetonitrile is described. Under these mild conditions other protecting groups such as acid sensitive allyl, benzyl, and Me3CPh2Si ethers, or isopropylidene acetals were unchanged. Interestingly, a selective alkoxy-PMB cleavage was observed in the presence of a PMB phenoxy ether.

Carbohydrate-Based Studies Toward the Synthesis of Hamigeromycin E: A Stereoselective Total Synthesis of an Isomer of Zeaenol

A stereoselective synthesis of 14-membered macrolide hamigeromycin E (6) has been studied by employing ortho-lithiated formylation, Barbier allylation, Julia–Kocienski olefination, Mitsunobu esterification, and ring-closing metathesis (RCM) reactions. The

Asymmetric total syntheses of cochliomycin A and zeaenol

The first asymmetric total syntheses of two resorcylic acid lactones (RALs) - cochliomycin A and zeaenol - have been achieved in a divergent way. The main highlight of our strategy involves successful application of stereoselecive Keck allylation and Julia-Kocienski olefination to access an advanced intermediate, by starting from L-tartaric acid as a chiral pool compound. This intermediate is coupled with a trisubstituted benzoic acid to afford a common RCM precursor for both target molecules. Ring-closing metathesis at a late stage, followed by functional group manipulation, yielded the target molecules in an efficient way. Two resorcylic acid lactones (RALs) - cochliomycin A and zeaenol - have been synthesized for the first time by an enantiodivergent route from the common chiral pool compound L-tartaric acid. Copyright

Chemo-enzymatic asymmetric total synthesis of stagonolide-C

The naturally occurring phytotoxic noneolide stagonolide-C has been synthesized by a chemo-enzymatic approach. Two key intermediates have been synthesized by applying a metal-enzyme combined DKR (dynamic kinetic resolution) strategy, followed by RCM (ring

The furan approach to oxacycles. Part 4: A synthesis of (+)-decarestrictine L

We describe an efficient new approach for the enantioselective synthesis of (+)-(2R,3S,6R)-decarestrictine L from commercially available starting material using our newly developed methodology based on the oxidation of a furan ring with singlet oxygen fol

Biomimetic synthesis of the pentacyclic nucleus of ptilomycin A

The methyl ester of the pentacyclic nucleus of ptilomycalin A (9) has been prepared by an efficient, convergent, biogenetic, 14-step route. The key steps involve the conversion of acyclic bis enone 39 to 9 in four steps. Michael addition of O-methylisourea to 39 afforded 52% of a mixture of isoureas 40 and 41, which were both converted to 72% of tricyclic aminals 42 and 43 by ammonolysis. Deprotection of the silyl ethers with HF and cyclization with Et3N in MeOH afforded 9 (~34% from 42) and the diastereomer 45 with an equatorial methyl ester group (~26% from 42).