1274953-68-2

Upstream product

• 1274953-66-0 tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate 
• 1208329-03-6 (S,E)-8-(4-methoxy-benzyloxy)-octa-1,5-dien-4-ol 
• 1274953-78-4 (S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol 
• 1274953-79-5 (3S,5S)-1-(4-methoxy-benzyloxy)-oct-7-ene-3,5-diol 
• 1274953-81-9 (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene 
• 1274953-67-1 (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al 
• 1274953-82-0 (R)-7-azido-4-[(tert-butyldimethylsilanyloxy)]-1-heptene 
• 1274953-83-1 tert-butyl ((4R)-4-{[tert-butyl(dimethyl)silyl]oxy}hept-6-en-1-yl)carbamate 
• 142860-83-1 1-(4-methoxybenzyloxy)-3-butene 
• 671232-57-8 (E)-5-(4-methoxy-benzyloxy)-pent-2-en-1-al 
• 1275575-88-6 N,N,N-tributylbutan-1-aminium trifluoro(propa-1,2-dien-1-yl)borate 
• 53915-69-8 allenyltributylstannane 
• 169517-16-2 2-allenyl-[1,3,2]-dioxaborinane 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 1329019-92-2 5.10.5. tert-butyl {(4R,6E,8S,10E,12S,14R,16S)-4,8,12,14,16-pentakis{[tert-butyl(dimethyl)silyl]oxy}-18-[(4-methoxybenzyl)oxy]octadeca-6,10-dien-1-yl}carbamate 

Relevant academic research and scientific papers

Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.

Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 in 72-98% yields with >95% ee and >20:1 dr. Application of this method to the synthesis of the tetrafibricin C(23)-C(40) fragment 19 is described.