Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst

2015 ◽  
Vol 54 (37) ◽  
pp. 10935-10939 ◽  
Author(s):  
Akira Nakagawa ◽  
Masamichi Tanaka ◽  
Shun Hanamura ◽  
Daisuke Takahashi ◽  
Kazunobu Toshima
Keyword(s):  
Stereoselective Glycosylation ◽  
Boronic Ester

ChemInform Abstract: Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst.

ChemInform ◽  
2016 ◽  
Vol 47 (3) ◽  
Author(s):  
Akira Nakagawa ◽  
Masamichi Tanaka ◽  
Shun Hanamura ◽  
Daisuke Takahashi ◽  
Kazunobu Toshima
Keyword(s):  
Stereoselective Glycosylation ◽  
Boronic Ester

Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst

2015 ◽  
Vol 127 (37) ◽  
pp. 11085-11089 ◽  
Author(s):  
Akira Nakagawa ◽  
Masamichi Tanaka ◽  
Shun Hanamura ◽  
Daisuke Takahashi ◽  
Kazunobu Toshima
Keyword(s):  
Stereoselective Glycosylation ◽  
Boronic Ester

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

“Solid-Liquid” Vitrimers Based on Dynamic Boronic Ester Networks

2021 ◽  
Author(s):  
Sheng Wang ◽  
Lu-Lu Xue ◽  
Xiao-Zhuang Zhou ◽  
Jia-Xi Cui
Keyword(s):  
Boronic Ester ◽  
Solid Liquid

Biobased, Biodegradable, Self-Healing Boronic Ester Vitrimers from Epoxidized Soybean Oil Acrylate

2020 ◽  
Author(s):  
Arkadiusz Zych ◽  
Jonathan Tellers ◽  
Laura Bertolacci ◽  
Luca Ceseracciu ◽  
Lara Marini ◽  
...  
Keyword(s):  
Soybean Oil ◽  
Epoxidized Soybean Oil ◽  
Self Healing ◽  
Boronic Ester

Enantioselective synthesis of (R)-tolterodine using lithiation/borylation–protodeboronation methodology

2012 ◽  
Vol 90 (11) ◽  
pp. 965-974 ◽  
Author(s):  
Stefan Roesner ◽  
Varinder K. Aggarwal
Keyword(s):  
Enantioselective Synthesis ◽  
High Yield ◽  
Magnesium Bromide ◽  
Efficient Synthesis ◽  
Boronic Ester ◽  
Better Than

The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation–protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee.

scholarly journals Stereoselective synthesis of glycosides using (salen)Co catalysts as promoters

2015 ◽  
Vol 51 (43) ◽  
pp. 8939-8941 ◽  
Author(s):  
Sandra Medina ◽  
Alexander S. Henderson ◽  
John F. Bower ◽  
M. Carmen Galan
Keyword(s):  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Co Catalysts ◽  
New Class ◽  
Stereoselective Glycosylation ◽  
Glycosyl Donors

The use of (salen)Co catalysts as a new class of bench-stable stereoselective glycosylation promoters of trichloroacetimidate glycosyl donors at room temperature is described.

Sign in / Sign up

Export Citation Format

Share Document