84588-33-0

Upstream product

• 1114-34-7 D-lyxose 
• 100-51-6 benzyl alcohol 
• 87-72-9 D-lyxose 
• 5328-37-0 L-arabinose 
• 87-72-9 L-arabinofuranose 

Downstream Products

• 84588-32-9 benzyl-(tri-O-acetyl-α-D-lyxopyranoside) 
• 103773-81-5 1-O-benzyl-2,3-isopropylidene-L-lyxopyranose 
• 71980-98-8 pseudomonic acid C 
• 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 
• 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 
• 89726-70-5 (3aR,7S,7aR)-7-(2-Benzenesulfonyl-ethyl)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 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 
• 209787-64-4 benzyl 2,3-O-isopropylidene-α-D-lyxopyranoside 
• 74491-81-9 benzyl 2,3-O-isopropylidene-β-L-erythro-pentopyranosid-4-ulose 

Relevant academic research and scientific papers

(5aR)-5a-C-Pentyl-4-epi-isofagomine: A powerful inhibitor of lysosomal β-galactosidase and a remarkable chaperone for mutations associated with GM1-gangliosidosis and Morquio disease type B

This report is about the identification, synthesis and initial biological characterization of derivatives of 4-epi-isofagomine as pharmacological chaperones (PC) for human lysosomal β-galactosidase. The two epimers of 4-epi-isofagomine carrying a pentyl group at C-5a, namely (5aR)- and (5aS)-5a-C-pentyl-4-epi-isofagomine, were prepared by an innovative procedure involving in the key step the addition of nitrohexane to a keto-pentopyranoside. Both epimers were evaluated as inhibitors of the human β-galactosidase: the (5aR)-stereoisomer (compound 1) was found to be a very potent inhibitor of the enzyme (IC50?=?8?nM, 30× more potent than 4-epi-isofagomine at pH 7.3) with a high selectivity for this glycosidase whereas the (5aS) epimer was a much weaker inhibitor. In addition, compound 1 showed a remarkable activity as a PC. It significantly enhanced the residual activity of mutant β-galactosidase in 15 patient cell lines out of 23, with enhancement factors greater than 3.5 in 10 cell lines and activity restoration up to 91% of normal. Altogether, these results indicated that (5aR)-5a-C-pentyl-4-epi-isofagomine constitutes a promising PC-based drug candidate for the treatment of GM1-gangliosidosis and Morquio disease type B.

4-EPI-ISOFAGOMINE DERIVATIVES

The present invention relates to 4-epi-isofagomine derivatives, pharmaceutically acceptable salts thereof, and the use of said 4-epi-isofagomine derivatives in the treatment and/or prevention of lysosomal storage diseases. The present invention is further

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.