18918-48-4

Upstream product

• 135-19-3 β-naphthol 
• 5160-09-8 2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride 
• 18918-47-3 2-naphthyl 2,3,4-triacetyl-α-L-rhamnose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 73-34-7 L-rhamnose 

Relevant academic research and scientific papers

Synthesis of aryl α-O-L-rhamnopyranoside by two-step reaction in one pot

The title compounds were conveniently synthesized by a phase transfer catalyzed approach in two steps and one pot using the rhamnopyranosyl chloride as key intermediate. The twostep one-pot procedure is more convenient and environmentally friendly, compared to the published synthetic routes. Besides, the structure-reactivity relationship and the plausible mechanism for this base-catalyzed glycosylation were discussed bymeans of the Hammett equation.

On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

Subtilisin-catalyzed esterification of several enatiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated.