Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 13, Issue -, Pages 1222-1229Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.13.121
Keywords
amino sugar; 3,6-anhydro-alpha-L-galactopyranose; polysaccharide (agar); protecting-group-free; reductive amination
Categories
Funding
- Fundacao Araucaria [15152]
- CAPES
- PRONEX-Carboidratos [14669]
Ask authors/readers for more resources
Agarose was herein employed as starting material to produce primary, secondary and tertiary C-glycoside glycamines, including mono-and disaccharide structures. The semisynthetic approach utilized was generally based on polysaccharide-controlled hydrolysis followed by reductive amination. All reactions were conducted in aqueous media and without the need of hydroxyl group protection. We were able to identify optimal conditions for the reductive amination of agar hydrolysis products and to overcome the major difficulties related to this kind of reaction, also extending it to reducing anhydrosugars. The excess of ammonium acetate, methyl-or dimethylamine, and the use of a diluted basic (pH 11) reaction media were identified as important aspects to achieve improved yields, as well as to decrease the amount of byproducts commonly related to reductive amination of carbohydrates. This strategy allowed the transposition of the 3,6-anhydro-alpha-L-galactopyranose unit (naturally present in the agarose structure) to all glycamines synthesized, constituting an amino-substituted C-threofuranoside moiety, which is closely related to (+)-muscarine.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available