290815-63-3

Upstream product

• 290815-55-3 2,2-bis-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithiane 
• 290815-56-4 6-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-7-(4-methoxy-benzyloxy)-hept-1-en-4-ol 
• 290815-57-5 5-(tert-butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3-hydroxy-6-(4-methoxy-benzyloxy)-hexanal 
• 290815-59-7 5-(tert-butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-en-1-ol 
• 290815-58-6 (R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-enal 
• 290815-54-2 (2R,6R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1,7-bis-(4-methoxy-benzyloxy)-heptan-4-one 
• 290815-60-0 3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol 
• 290815-69-9 (R)-4-[(R)-2-Hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxymethyl)-5,6-dihydro-pyran-2-one 
• 108-94-1 cyclohexanone 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 290815-62-2 (R)-4-[(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)methyl]-6-hydroxymethyl-5,6-dihydro-pyran-2-one 

Downstream Products

• 290815-66-6 (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-[(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)methyl]-1-(4-methoxy-benzyloxy)-hex-4-en-2-ol 
• 290815-68-8 Methanesulfonic acid (2R,6R)-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2,6-dihydroxy-7-(4-methoxy-benzyloxy)-heptyl ester 
• 290815-67-7 (2R,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-7-(4-methoxy-benzyloxy)-heptane-1,2,6-triol 
• 290815-52-0 [(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol 
• 290815-53-1 (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-4-(R)-1-oxiranylmethyl-hex-4-en-2-ol 
• 290815-64-4 (E)-(R)-3-[(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)methyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol 

Relevant academic research and scientific papers

Control of olefin geometry in the bryostatin B-ring through exploitation of a C2-symmetry breaking tactic and a Smith-Tietze coupling reaction

(equation presented) A completely stereocontrolled asymmetric synthesis of an advanced B-ring synthon for the bryostatin family of antitumor agents is reported. Noteworthy features of our synthesis include the Smith-Tietze bis-alkylation reaction between 12 and 13 en route to C2-symmetrical ketone 10 and the totally stereoselective conversion of 10 into triol 18 via a Grignard addition tactic. Triol 18 was converted to epoxide 3 in nine steps, and an acid-catalyzed intramolecular Williamson etherification reaction completed the synthesis of 2.