121352-86-1

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 38216-93-2 3-benzyloxypivalic aldehyde 
• 623-73-4 diazoacetic acid ethyl ester 
• 66582-32-9 3-(benzyloxy)-2,2-dimethylpropan-1-ol 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 121352-87-2 (E)-5-(benzyloxy)-4,4-dimethylpent-2-en-1-ol 
• 130199-57-4 ((2S,3S)-3-(1-(benzyloxy)-2-methylpropan-2-yl)oxiran-2-yl)methanol 
• 215317-64-9 (3R,5R)-5-(1-(tert-butyldiphenylsilyloxy)-2-methylpropan-2-yl)-3-methyldihydrofuran-2(3H)-one 
• 187527-24-8 (2S,3S,4R,7S)-1-benzyloxy-7,9-bis(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6,6-tetramethylnonan-5-one 
• 187527-27-1 (3S,6R,7S,8S)-9-benzyloxy-1,3,7-trihydroxy-4,4,6,8-tetramethylnonan-5-one 
• 187527-25-9 (-)-(5S)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethylheptan-3-one 
• 187527-29-3 [(S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentyloxymethyl]-benzene 
• 152426-81-8 (3S)-1-benzyloxy-2,2-dimethylpentane-3,5-diol 
• 121352-88-3 [(2R,3R)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-methanol 

Relevant academic research and scientific papers

Stereoselective Synthesis of γ-Butyrolactones Subunit of Polycavernoside A

An efficient and versatile linear synthesis of γ-butyrolactone subunit of polycavernolide A has been reported in 14.2% overall yield with 10 linear steps by employing Sharpless asymmetric epoxidation, ring-closing metathesis, and diastereoface selective h

Diazo reagents in copper(I)-catalyzed olefination of aldehydes

The olefination of aldehydes to synthesize unsaturated ketones, esters, amides and phosphonates using diazo reagents and triphenylphosphine in the presence of copper(I) iodide as catalyst, is described. Good to excellent E:Z selectivities as well as yields were obtained for a large variety of aliphatic, aromatic and heteroaromatic aldehydes. The reaction showed also an excellent functional group compatibility and aldehydes were selectively reacted in the presence of ketone, nitro, amine, ether, acetal, thioether and halide groups. The use of a cost-effective copper salt as a catalyst is advantageous compared to previously reported expensive transition metal complexes. The method was used in the total synthesis of the scutifoliamide A, a biologically active compound that exhibits antifungal activity.

The formal total synthesis of epothilone A

The formal total synthesis of epothilone A is described. The key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reaction (RCM) and the diastereoselective alkylation at C8. Aldehyde 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An efficient route to keto acid 5 is described.

Synthesis of the C1-C9 segment of epothilons

The C1-C9 segment of epothilons was generated by an aldol reaction between chiral aldehyde 3 and ethyl ketone 4. Removal of the TBS protecting groups and debenzylation generated spiro ketal 13 which was analyzed by X-ray crystallography.