207602-68-4

Upstream product

• 98-88-4 benzoyl chloride 
• 39946-32-2 methyl 2-O-benzyl-6-deoxy-β-D-galactopyranoside 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 207602-70-8 methyl 3-O-benzoyl-2-O-benzyl-6-deoxy-β-D-galactopyranoside 

Downstream Products

• 207602-74-2 Benzoic acid (2R,3R,4S,5R,6R)-3-benzyloxy-2-methoxy-6-methyl-5-((1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-tetrahydro-pyran-4-yl ester 
• 207681-90-1 Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester 
• 207681-89-8 methyl 4,6-dideoxy-4-[(1'R,4'R,5'S,6'S)-4',5',6'-trihydroxy-3'-(hydroxymethyl)cyclohex-2'-enyl]amino-β-D-glucopyranoside 

Relevant academic research and scientific papers

The synthesis of a diastereoisomer of methyl acarviosin

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.