89824-53-3

Upstream product

• 67-64-1 acetone 
• 112348-40-0 benzyl 4-<2-(phenylsulfonyl)ethyl>-4-deoxy-β-L-lyxopyranoside 
• 18403-20-8 benzyl 2-O-benzoyl-α-D-xylopyranoside 
• 18403-12-8 benzyl β-D-xylopyranoside 
• 112348-39-7 benzyl 4-<2-(phenylsulfonyl)ethyl>-4-deoxy-2,3-di-O-benzoyl-β-L-lyxopyranoside 
• 112348-35-3 benzyl 4-bromo-4-deoxy-2,3-di-O-benzoyl-β-L-lyxopyranoside 
• 100-51-6 benzyl alcohol 
• 89726-66-9 Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester 
• 97997-35-8 Methanesulfonic acid 2-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethyl ester 
• 89726-69-2 2-((3aR,7S,7aR)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethanol 
• 83160-44-5 (3aR,7S,7aR)-7-Allyl-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 3111-52-2 potassium thiophenolate 
• 87-72-9 L-arabinofuranose 
• 103773-81-5 1-O-benzyl-2,3-isopropylidene-L-lyxopyranose 

Downstream Products

• 89726-72-7 Methanesulfonic acid (2S,3S)-1-[1-benzenesulfonyl-2-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyl ester 
• 71980-98-8 pseudomonic acid C 
• 89726-71-6 (4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol 

Relevant academic research and scientific papers

An Approach to Pseudomonic Acids from D-Xylose

The four contiguous chiral centers present in pseudomonic acid C are constructed in an efficient way from D-xylose.The key steps involve a highly selective intermolecular radical reaction between benzyl 4-bromo-4-deoxy-2,3-di-O-benzoyl-β-L-lyxopyranoside (9) and phenyl vinyl sulfone for incorporating the lower appendage and a stereoselective intramolecular Michael addition to achieve the correct stereochemistry at the anomeric site.

Pseudomonic Acid C from L-Lyxose

Full details of the total synthesis of pseudomonic acid C from L-lyxose are described.Key features of the approach involve feee-radical allylation for stereoselective C-C bond formation at C4 of lyxose, Frater alkylation to generate correct stereochemistry at C12 and C13, and stereoselective intramolecular Michael addition to establish the correct stereochemistry of the "anomeric" appendage.

Total Synthesis of Pseudomonic Acid C

A convergent total synthesis of pseudomonic acid C from L-lyxose is described in which a highly stereoselective free-radical C-C bond construction plays a key role.