192372-86-4Relevant academic research and scientific papers
The synthesis of a diastereoisomer of methyl acarviosin
McAuliffe, Joseph C.,Stick, Robert V.,Tilbrook, D. Mathew G.,Watts, Andrew G.
, p. 91 - 95 (2007/10/03)
In model studies, a fully protected D-galactopyranoside 4-triflate and two 6-deoxy analogues were shown to alkylate cyclohexylamine, leading to 4-cyclohexylamino-4-deoxy- and 4,6-dideoxy-D-glucopyranosides as the major products in satisfactory yield, accompanied by alkenes resulting from elimination of triflic acid. Coupling of tetra-O-benzyl-l-epivalienamine with methyl 3- O-benzoyl-6-deoxy-4-O-trifluoromethylsulfonyl-β-D-galactoside gave a diastereoisomer of methyl acarviosin in protected form. Deprotection completed the first synthesis of methyl 4,6-dideoxy-4-[(l′R,4′R,5′ S,6′S)-4′,5′,6′-trihydroxy3′-(hydroxymethyl) cyclohex-2′-enyl]amino-β-D-glucoside, a potential β-glycosidase inhibitor.
A new route to D-xylo-hexo-5-ulose and some of its selectively protected derivatives from D-galactose(
Barili, Pier Lugi,Berti, Giancarlo,Catelani, Giorgio,D'Andrea, Felicia,De Rensis, Francesco
, p. 8665 - 8674 (2007/10/03)
A new approach to D-xylo-hexos-5-ulose, a useful synthetic intermediate, is described, starting from methyl β-D-galactopyranoside and involving as the key step an epoxidation/methanolysis of 3-O-protected methyl 2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-eno
