An efficient synthesis of a C₁₂-higher sugar aminoalditol

Abstract

The C12-aminoalditol H2NCH2–(CHOBn)10–CH2OH was prepared from two simple monosaccharide building blocks. The synthesis was realized by a regioselective introduction of the azide group and subsequent protection–deprotection transformations. The chemical reactivity of the aminoalditol was tested in the reductive amination reaction with a selectively protected sucrose monoaldehyde.

Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"

“…Aldehyde 20 [ 37 ] – obtained by Swern oxidation [ 38 ] of alcohol 19 – was reacted with amine 17 to afford the desired amine isolated as acetate 21 in 85% total yield. Removal of the TBDPS protecting group from the C6’-position gave alcohol 22 in 97% yield.…”

“…A solution of amine 17 (203 mg, 0.72 mmol) in DCM (10 mL) was added to a solution of aldehyde 20 (202 mg, 0.18 mmol; prepared from alcohol 19 as described in our previous paper [ 37 ]) in DCM (10 mL) containing acetic acid (41 μL, 0.72 mmol) and MgSO 4 (≈200 mg), and the mixture was stirred for 1 h at rt. Then, NaBH 3 CN (17 mg, 0.72 mmol) was added and stirring was continued overnight.…”

New bio-amphiphilic structures of sucrose via amides linkages

“…The availability, biodegradability, solubility and functionality make sucrose great starting material for numerous of transformational reactions achieved by chemist and researchers to handle the access in sucrose production and ind other sucrose analogs with new medical and industrial applications (Queneau et al, 2007). Szyszka and co-workers were able to transform sucrose by coupling with a higher amino alditol pendant C −6 of glucose moiety (Szyszka et al, 2017). Potewar and et al were obtained 1,2,3-triazole-sucrose derivatives by applied cycloaddition reaction on sucrose azides and terminal alkynes as antimicrobial, anti fungi derivatives (Potewar et al, 2013).…”