1329019-92-2

Upstream product

• 671232-57-8 (E)-5-(4-methoxy-benzyloxy)-pent-2-en-1-al 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 1274953-68-2 tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate 
• 1274953-83-1 tert-butyl ((4R)-4-{[tert-butyl(dimethyl)silyl]oxy}hept-6-en-1-yl)carbamate 
• 1274953-82-0 (R)-7-azido-4-[(tert-butyldimethylsilanyloxy)]-1-heptene 
• 1274953-66-0 tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate 
• 1274953-67-1 (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al 
• 1274953-81-9 (3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-oct-7-ene 
• 1274953-79-5 (3S,5S)-1-(4-methoxy-benzyloxy)-oct-7-ene-3,5-diol 
• 1274953-78-4 (S)-1-((2S,3S)-3-(2-(4-methoxy-benzyloxy)-ethyl)oxiran-2-yl)-but-3-en-1-ol 
• 1208329-03-6 (S,E)-8-(4-methoxy-benzyloxy)-octa-1,5-dien-4-ol 

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.