84588-33-0

Basic information

• Product Name: benzyl α-D-lyxopyranoside
• Synonyms: benzyl α-D-lyxopyranoside
• CAS NO: 84588-33-0
• Molecular Weight: 240.256
• Mol File: 84588-33-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: benzyl α-D-lyxopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl α-D-lyxopyranoside(84588-33-0)
• EPA Substance Registry System: benzyl α-D-lyxopyranoside(84588-33-0)

Safety Data

• Hazardous Substances Data: 84588-33-0(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 84588-32-9 benzyl-(tri-O-acetyl-α-D-lyxopyranoside) 
• 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 
• 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 
• 103773-81-5 1-O-benzyl-2,3-isopropylidene-L-lyxopyranose 

Relevant articles and documents

(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.

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.