466680-65-9

Upstream product

• 186581-53-3 diazomethane 
• 466680-62-6 5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal 
• 264919-23-5 4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 
• 466680-59-1 Acetic acid (1R,2R)-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-hydroxymethyl-ethyl ester 
• 466680-61-5 Acetic acid (1S,2S)-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-formyl-ethyl ester 

Downstream Products

• 466680-66-0 methyl 4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronate dimethyl acetal 

Relevant academic research and scientific papers

Chemical transformation of lactose into 4-O-beta-D-galactopyranosyl-D-glucuronic acid (pseudolactobiouronic acid) and some derivatives thereof.

The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2',6'-di-O-benzyl-2,3:3',4'-di-O-isopropylidenelactose dimethyl acetal (1) through a simple multi-step procedure based on the selective acetylation of OH-5 of 1 (methoxyisopropylation, acetylation, de-methoxyisopropylation) followed by a two-step oxidation at C-6 (TPAP-NMO then TEMPO-NaOCl) and finally, complete removal of the protecting groups.