91020-91-6

Upstream product

• 4541-14-4 4-benzyloxy-butan-1-ol 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 5470-84-8 4-benzyloxybutanal 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 150760-92-2 3-(3-benzyloxy-propyl)-<1.2.4>-trioxolane 
• 141-82-2 malonic acid 
• 100-39-0 benzyl bromide 
• 180963-90-0 6-benzyloxy-2(Z)-hexenoic acid methyl ester 
• 81518-74-3 1-benzyloxy-4-pentene 

Downstream Products

• 219700-38-6 Methyl (3S)-3-{N-benzyl-N-[(S)-1-phenylethyl]amino}-6-benzyloxyhexanoate 
• 219700-39-7 (2R,3R)-3-{(S)-4-Benzyloxy-1-[benzyl-((S)-1-phenyl-ethyl)-amino]-butyl}-2-hydroxy-2-methyl-succinic acid dimethyl ester 
• 219700-40-0 (2S,3R)-3-{(S)-4-Benzyloxy-1-[benzyl-((S)-1-phenyl-ethyl)-amino]-butyl}-2-hydroxy-2-methyl-succinic acid dimethyl ester 
• 91020-97-2 3a,6a-Bis-(2-benzyloxy-ethyl)-2,5-dihydroxy-3,6-dioxo-3,3a,3b,6,6a,6b-hexahydro-cyclobutadicyclopentene-1,4-dicarboxylic acid dimethyl ester 
• 78132-75-9 6-benzyloxy-hexanoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of the DEF-bis-spiroacetal of spirastrellolide a exploiting a double asymmetric dihydroxylation/spiroacetalisation strategy

An efficient synthesis of the C26-C40 tricyclic [5,6,6]-bis-spiroacetal segment of the marine macrolide spirastrellolide A has been developed, exploiting a novel double Sharpless asymmetric dihydroxylation/spiroacetalisation sequence. The Royal Society of Chemistry 2006.

Syntheses of α,β-unsaturated carbonyl compounds from the reactions of monosubstituted ozonides with stable phosphonium ylides

Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-αβ-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-αβ-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position of the heteroatom in the substituent of the ozonides. The possible mechanism of this reaction will be discussed. (C) 2000 Elsevier Science Ltd.

β-Amino ester route to tussilagine, isotussilagine and (-)-petasinecine

Condensation of enantiopure β-amino ester 2a with methyl pyruvate provides two diastereoisomers 3 and 4. Both 3 and 4 are subjected to hydrogenation followed by cyclization producing pyrrolidinones 5 and 8. From 5 and 8 isotussilagine and tussilagine are obtained respectively, by using a Mitsunobu reaction as a key step. In a similar manner, (-)-petasinecine is synthesized from the condensation product of 2b with ethyl glyoxalate.

Enantioselective synthesis of tussilagine and isotussilagine

Tussilagine and isotussilagine are synthesized through the coupling reactions of N,N-disubstituted β-amino-esters with methyl pyruvate and Mitsunobu reactions as key steps.

Stereoselective Construction of Copaborneol and Longiborneol Frameworks by Intramolecular Double Michael Reaction

Stetreoselective synthesis of tricyclo3,8>decane 22 and tricyclo3,9>undecane 26 the basic skeleton of copaborneol and longiborneol, were achieved by the intramolecular double Michael reactions of 2-cyclopenten-1-ones 15-17.The substrates were prepared starting with tricyclo2,6>deca-4,8-dien-3-one (6).The intramolecular double Michael reactions were carried out under three different conditions: TMSCl-Et3N-ZnCl2.TMSI-(TMS)2NH, and Bu2BOTf-(TMS)2NH.The framework 26 of longiborneol was constructed in good yield using the latter two reagent systems.