155681-03-1

Basic information

• Product Name: benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside
• Synonyms: benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside
• CAS NO: 155681-03-1
• Molecular Weight: 278.305
• Mol File: 155681-03-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside(155681-03-1)
• EPA Substance Registry System: benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside(155681-03-1)

Safety Data

• Hazardous Substances Data: 155681-03-1(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 50-69-1 D-ribose 
• 23276-32-6 benzyl 2,3-O-isopropylidene-D-ribofuranoside 

Downstream Products

• 155793-68-3 2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione 
• 471-62-5 hopane 
• 448926-96-3 N-hexyl-1,5-dideoxy-1,5-iminoribitol 

Relevant articles and documents

N-Alkyl-, 1-C-Alkyl-, and 5-C-Alkyl-1,5-dideoxy-1,5-imino-(l)-ribitols as Galactosidase Inhibitors

A series of 1,5-dideoxy-1,5-imino-(l)-ribitol (DIR) derivatives carrying alkyl or functionalized alkyl groups were prepared and investigated as glycosidase inhibitors. These compounds were designed as simplified 4-epi-isofagomine (4-epi-IFG) mimics and were expected to behave as selective inhibitors of β-galactosidases. All compounds were indeed found to be highly selective for β-galactosidases versus α-glycosidases, as they generally did not inhibit coffee bean α-galactosidase or other α-glycosidases. Some compounds were also found to be inhibitors of almond β-glucosidase. The N-alkyl DIR derivatives were only modest inhibitors of bovine β-galactosidase, with IC50 values in the 30-700 μm range. Likewise, imino-l-ribitol substituted at the C1 position was found to be a weak inhibitor of this enzyme. In contrast, alkyl substitution at C5 resulted in enhanced β-galactosidase inhibitory activity by a factor of up to 1000, with at least six carbon atoms in the alkyl substituent. Remarkably, the 'pseudo-anomeric' configuration in this series does not appear to play a role. Human lysosomal β-galactosidase from leukocyte lysate was, however, poorly inhibited by all iminoribitol derivatives tested (IC50 values in the 100 μm range), while 4-epi-IFG was a good inhibitor of this enzyme. Two compounds were evaluated as pharmacological chaperones for a GM1-gangliosidosis cell line (R301Q mutation) and were found to enhance the mutant enzyme activity by factors up to 2.7-fold.

Simple Approach to O-Protected Deaminotunicaminyluracil

A five-step synthesis of deaminotunicaminyluracil is presented.Coupling of the ylide, generated from the phosphonium salt 4, with the aldehyde 5 afforded the undecose 6 in high yield.The key step in this synthesis was the hydroboration-oxidation reaction of the olefin 6.For this purpose several hydroborating reagents were examined.The diborane-THF reagent led to the desired deaminotunicamine derivative 8, as the predominant product.Condensation of undecose 8c with 1,3-di-O-trimethylsilyluracil gave the title compound.