
TY  - JOUR
A1  - McAuliffe, Joseph C. 
A1  - Stick, Robert V. 
A1  - Tilbrook, D. Matthew G. 
A1  - Watts, Andrew G. 
T1  - The Synthesis of a Diastereoisomer of Methyl Acarviosin
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1998
VL  - 51
IS  - 2
SP  - 91
EP  - 96
KW  - 
UR  - https://doi.org/10.1071/C97153 
N2  - 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-1-epivalienamine with methyl 3-O-benzoyl-6-deoxy-4-O- trifluoromethylsulfonyl-&#946;-D-galactoside gave a diastereoisomer of methyl acarviosin in protected form. Deprotection completed the first synthesis of methyl 4,6-dideoxy-4-&#91;(1&#8242;R,4&#8242;R,5&#8242;S,6&#8242;S)-4&#8242;,5&#8242;,6&#8242;-trihydroxy-3&#8242;-(hydroxymethyl)cyclohex-2&#8242;-enyl&#93;amino-&#946;-D-glucoside, a potential &#946;-glycosidase inhibitor. 
ER  -

