504422-22-4Relevant academic research and scientific papers
Synthesis of 5a,5a′-dicarba-D-glucobioses from conformationally restricted carbaglucosyl triflates using SN2-type inversion with carbaglucosyl nucleophiles
Tateda, Naoya,Ajisaka, Katsumi,Ishiguro, Masaji,Miyazaki, Tatsuo
, p. 2345 - 2367 (2019/01/04)
Novel carbohydrate mimics were designed which contain two 5a-carba-D-glucose residues, one each at reducing and nonreducing end, and thus these mimics are 5a,5a′-dicarba-D-glucobioses. Dicarbadisaccharides have attractive features such as stability agains
Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside
Ogawa, Seiichiro,Aoyama, Hiroshi,Sato, Toshinori
, p. 1979 - 1992 (2007/10/03)
For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.
