917871-11-5

Upstream product

• 917871-10-4 (R)-(E)-(+)-ethyl-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenoate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 95514-03-7 (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester 
• 95514-04-8 (R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 
• 92817-88-4 (2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal 

Downstream Products

• 917871-09-1 (4R)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenal 
• 1035677-71-4 ((2S,3S)-3-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)oxiran-2-yl)methanol 
• 164907-39-5 (4R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-4-methylpentan-1-ol 
• 1352126-06-7 C₃₃H₄₄O₄Si 
• 1352125-86-0 (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4⁽⁵⁾-ene 
• 412908-67-9 (3R,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpent-1-en-3-ol 
• 603994-09-8 (2R,3R)-3-methoxy-5-(4'-methoxybenzyloxy)-2-methylpentanal 
• 301230-10-4 (3R,4S)-5-(tert-butyldiphenylsilyloxy)-3-methoxy-4-methylpentan-1-ol 

Relevant academic research and scientific papers

Approaches towards the total synthesis of carolacton: Synthesis of C1-C16 fragment

Abstract A stereoselective synthesis of the C1-C16 segment of biofilm inhibitor carolacton has been achieved. The synthetic strategy involves Sharpless asymmetric epoxidation, Roush crotylation, Steglich esterification, RCM reaction and selective reduction of a disubstituted olefin in the presence of a trisubstituted olefin using in situ generated diimide.

Studies culminating in the total synthesis and determination of the absolute configuration of (-)-saudin

A full account of studies that culminated in the total synthesis of both antipodes and the assignment of its absolute configuration of Saudin, a hypoglycemic natural product. Two approaches are described, the first proceeding though bicyclic lactone intermediates and related second monocyclic esters. The former was obtained via asymmetric Diels-Alder cycloaddition and the latter by an asymmetric annulation protocol. Both approaches employ a Lewis acid promoted Claisen rearrangement, with the successful approach taking advantage of bidentate chelation to control the facial selectivity of the key Claisen rearrangement.

Formal total synthesis of (-)-spongidepsin

The formal total synthesis of (-)-spongidepsin is described. Three fragments I, II, and III were first prepared from readily available starting materials and then assembled to the target compound. The key steps involved in the synthesis are asymmetric α-hydroxylation, Ender's alkylation, and ring-closing metathesis reactions. An alternative route for the fragment II is also achieved involving Sharpless asymmetric epoxidation and Gilman's alkylation as key reactions.

Palladium- and copper-catalyzed 1,4-additions of organozinc compounds to conjugated aldehydes

Conjugated aldehydes undergo smooth Pd(OAc)2·PPh 3- or Me2CuCNLi2-catalyzed 1,4-addition of dialkylzinc reagents.