143916-27-2

Upstream product

• 100-39-0 benzyl bromide 
• 104477-38-5 methyl 2-O-benzyl-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-galactopyranoside 
• 104530-14-5 Methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-galactopyranoside 
• 104477-38-5 (3aS,4R,6R,7R,7aS)-7-Benzyloxy-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 104530-15-6 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 
• 81348-26-7 methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside 

Relevant academic research and scientific papers

A new synthesis of L-ascorbic acid from D-galactose

1,5-Anhydro-D-galactitol, easily available from D-galactose, was selectively protected in positions 2, 3 and 4 and converted into 5-O-acetyl-2,6-anhydro-3-deoxy-L-threo-hex-2-enonic acid methyl ester, which, on reaction with MCPBA in acetic acid gave 2,5-di-O-acetyl-α-L-lyxo-hex-2-ulopyranosonic acid methyl ester. Reaction of the latter with sodium methoxide produced sodium L-ascorbate in high yield. Several side-reactions and the conformations of some of the intermediates are also discussed.