470-31-5

Upstream product

• 94840-87-6 methyl 5,O⁴-dimethyl-β-L-xylo-6-deoxy-hexopyranoside 
• 1602491-88-2 (R)-4-(allyloxy)-3-(methoxymethoxy)-4-methylpent-1-ene 
• 1602491-89-3 (R)-5-(methoxymethoxy)-6,6-dimethyl-3,4-dihydropyran-2-one 
• 1602491-90-6 (R)-5-Hydroxy-6,6-dimethyl-3,4-dihydropyran-2-one 
• 1005773-93-2 (5R)-5-methoxy-6,6-dimethyl-5,6-dihydro-2H-pyran-2-ol 
• 1005773-88-5 (R)-5-methoxy-6,6-dimethyl-5,6-dihydropyran-2-one 
• 1602491-86-0 (R)-3-(methoxymethoxy)-2-methylpent-4-ene-2-ol 
• 1602491-87-1 (R)-3-[(methoxymethoxy)-2-methylpent-4-en-2-yl]acrylate 

Downstream Products

• 200726-70-1 phenylmethyl-6-deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranoside 
• 229307-62-4 ethyl 7-((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)-oxy)-8-methyl-2-oxo-4-(phenylmethoxy)-2H-1-benzopyran-3-carboxylate 

Relevant academic research and scientific papers

Metathesis-Based de Novo Synthesis of Noviose

The rare carbohydrate L-(+)-noviose was synthesized from enantiomerically pure L-lactate. The configuration at C-4 was established by diastereoselective nucleophilic addition to an in-situ-generated lactaldehyde. The resulting homoallylic alcohol was further transformed into a set of ring-closing metathesis (RCM) precursors. These compounds were converted into noviose in few steps using RCM and RCM-allylic-oxidation sequences.

Metathesis-based de novo synthesis of noviose

The rare carbohydrate L-(+)-noviose was synthesized from enantiomerically pure L-lactate. The configuration at C-4 was established by diastereoselective nucleophilic addition to an in-situ-generated lactaldehyde. The resulting homoallylic alcohol was further transformed into a set of ring-closing metathesis (RCM) precursors. These compounds were converted into noviose in few steps using RCM and RCM-allylic-oxidation sequences. S-Ethyl lactate was converted into an enantiomerically pure tertiary homoallylic alcohol, which was then transformed into noviose using olefin metathesis reactions. Copyright