Uploaded March 2025 | Updated September 2026, 2 weeks ago
Ketals and acetals are more than protecting groups - they are some of the most versatile intermediates, as long as you know a few tricks to activate them.
In this video, I share a creative way to prepare nucleoside derivatives (important antiviral small molecule therapeutics), I also discuss ways to displace alkoxy groups of acetals & ketals with bromide, through the use of acyl bromides. Finally I discuss the Vasella reaction, a way to prepare functional-group-rich alkenes, through the elimination of bromides and iodides alpha to an acetal, using zinc.
Interested in synthetic consulting? Get in touch! More info at the end of the video. Interested sponsors are also encouraged to reach out.
Important Papers covers various chemical reactions, mechanisms, and research papers in the field of organic chemistry, providing examples and explanations for each research paper.
Support the Channel on Patreon - patreon.com/thatchemist
Important Papers Playlist - youtube.com/playlist?list=PL6OLqxmk7RtyRkdJhXK8NWpT1krGNq1p4
Meanwell Lab: meanwellresearchlab.com
Mike Meanwell plays Liszt - Un Sospiro: youtube.com/watch?v=Nw_bbQWaBbU
References:
Meanwell Nucleoside Paper: nature.com/articles/s41467-024-51520-5
ketoacetal bromodemethoxylation: doi.org/10.1021/ol991386p
tribromide: doi.org/10.1021/jo991822l
benzyl methoxybromide: doi.org/10.1002/jlac.19324980107
aryl ketoacetal bromodemethoxylation: doi.org/10.1002/jlac.19687160112
fluoride-containing: dx.doi.org/10.3762/bjoc.10.173
troc pyranose: dx.doi.org/10.1134/S1068162015020120
acetyl bromide eeros: doi.org/10.1002/047084289X.ra024
bromoacylation of ketones: pubs.acs.org/doi/10.1021/ja01436a036
1st vasella: doi.org/10.1016/j.tet.2016.10.038
N-Boc vasella: doi.org/10.1055/s-0041-1737335
Paclitaxel intermediate: doi.org/10.1021/jo981749j
slide 23: doi.org/10.1039/P19870001793
antibiotics: doi.org/10.1016/S0040-4020(01)96261-1
statin: doi.org/10.1021/ol035036l
pyranose opening: patents.google.com/patent/EP1589023A1/en?oq=EP1589023A1
thf-containing: doi.org/10.1021/jo991392z
carbamate vasella: doi.org/10.3987/com-95-7288
chloride vasella: doi.org/10.1002/hlca.19620450727
Ketals and acetals are more than protecting groups - they are some of the most versatile intermediates, as long as you know a few tricks to activate them.
In this video, I share a creative way to prepare nucleoside derivatives (important antiviral small molecule therapeutics), I also discuss ways to displace alkoxy groups of acetals & ketals with bromide, through the use of acyl bromides. Finally I discuss the Vasella reaction, a way to prepare functional-group-rich alkenes, through the elimination of bromides and iodides alpha to an acetal, using zinc.
Interested in synthetic consulting? Get in touch! More info at the end of the video. Interested sponsors are also encouraged to reach out.
Important Papers covers various chemical reactions, mechanisms, and research papers in the field of organic chemistry, providing examples and explanations for each research paper.
Support the Channel on Patreon - patreon.com/thatchemist
Important Papers Playlist - youtube.com/playlist?list=PL6OLqxmk7RtyRkdJhXK8NWpT1krGNq1p4
Meanwell Lab: meanwellresearchlab.com
Mike Meanwell plays Liszt - Un Sospiro: youtube.com/watch?v=Nw_bbQWaBbU
References:
Meanwell Nucleoside Paper: nature.com/articles/s41467-024-51520-5
ketoacetal bromodemethoxylation: doi.org/10.1021/ol991386p
tribromide: doi.org/10.1021/jo991822l
benzyl methoxybromide: doi.org/10.1002/jlac.19324980107
aryl ketoacetal bromodemethoxylation: doi.org/10.1002/jlac.19687160112
fluoride-containing: dx.doi.org/10.3762/bjoc.10.173
troc pyranose: dx.doi.org/10.1134/S1068162015020120
acetyl bromide eeros: doi.org/10.1002/047084289X.ra024
bromoacylation of ketones: pubs.acs.org/doi/10.1021/ja01436a036
1st vasella: doi.org/10.1016/j.tet.2016.10.038
N-Boc vasella: doi.org/10.1055/s-0041-1737335
Paclitaxel intermediate: doi.org/10.1021/jo981749j
slide 23: doi.org/10.1039/P19870001793
antibiotics: doi.org/10.1016/S0040-4020(01)96261-1
statin: doi.org/10.1021/ol035036l
pyranose opening: patents.google.com/patent/EP1589023A1/en?oq=EP1589023A1
thf-containing: doi.org/10.1021/jo991392z
carbamate vasella: doi.org/10.3987/com-95-7288
chloride vasella: doi.org/10.1002/hlca.19620450727
