99663-50-0

Basic information

• Product Name: 2,3-O,O-dibenzyl-6-O-tosyl-L-ascorbic acid
• Synonyms: 2,3-O,O-dibenzyl-6-O-tosyl-L-ascorbic acid
• CAS NO: 99663-50-0
• Molecular Weight: 510.565
• Mol File: 99663-50-0.mol

Chemical Properties

• CAS DataBase Reference: 2,3-O,O-dibenzyl-6-O-tosyl-L-ascorbic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O,O-dibenzyl-6-O-tosyl-L-ascorbic acid(99663-50-0)
• EPA Substance Registry System: 2,3-O,O-dibenzyl-6-O-tosyl-L-ascorbic acid(99663-50-0)

Safety Data

• Hazardous Substances Data: 99663-50-0(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 99663-32-8 (2R)-3,4-dibenzyloxy-2-[(1S)-1,2-dihydroxyethyl]-2H-furan-5-one 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 50-81-7 ascorbic acid 
• 2871-84-3 (R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one 

Relevant articles and documents

Crystal structures, circular dichroism spectra and absolute configurations of some L-ascorbic acid derivatives

Chiral 2,3-O,O-dibenzyl ethers of L-ascorbic acid with 4-(5,6-epoxy)- (4) and 6-O-tosyl- (8) functional groups were studied by X-ray crystallography and circular dichroism (CD) spectroscopy. The stereostructure of 2,3-O,O-dibenzyl-5,6-isopropylidene-L-ascorbic acid (6) and 8 was determined by X-ray crystal structure analysis. Comparison of the CD-spectra of 4 and 8 with the CD-spectra of their synthetic precursors (2-3, 5-7) and L-ascorbic acid (1) itself, as well as crystal structures of 6 and 8 permitted to deduce the absolute configuration of 4. Thus, the chiral atoms C-4 and C-5 in 4 have R and S configurations, which is consistent with the configuration of 1.

Antitumor and antiviral activities of 4-substituted 1,2,3-triazolyl-2,3-dibenzyl-L-ascorbic acid derivatives

Two series of 6-(1,2,3-triazolyl)-2,3-dibenzyl-L-ascorbic acid derivatives with the hydroxyethylene (8a?8u) and ethylidene linkers (10c?10p) were synthesized and evaluated for their antiproliferative activity against seven malignant tumor cell lines and antiviral activity against a broad range of viruses. Conformationally unrestricted spacer between the lactone and 1,2,3-triazole units in 8a?8u series had a profound effect on antitumor activity. Besides, the introduction of a long side chain at C-4 of 1,2,3-triazole that led to the synthesis of decyl-substituted 2,3-dibenzyl-L-ascorbic acid 8m accounted for a selective and potent antiproliferative activity on breast cancer MCF-7 cells cells in the nM range. Further analysis showed that compound 8m strongly enhanced expression of hypoxia inducible transcription factor 1 α (HIF-1α) and to some extent decreased expression of nitric oxide synthase 2 (NOS2) suggesting its role in regulating HIF-1α signalling pathway. The p-methoxyphenyl-substituted derivative 10g displayed specific anti-cytomegalovirus (CMV) potential, whereas aliphatic-substituted derivatives 8l and 8m had the most potent, yet relatively non-specific, anti-varicella-zoster (VZV) activity.

Design, synthesis and biological evaluation of novel l-ascorbic acid-conjugated pentacyclic triterpene derivatives as potential influenza virus entry inhibitors

Since the influenza viruses can rapidly evolve, it is urgently required to develop novel anti-influenza agents possessing a novel mechanism of action. In our previous study, two pentacyclic triterpene derivatives (Q8 and Y3) have been found to have anti-influenza virus entry activities. Keeping the potential synergy of biological activity of pentacyclic triterpenes and l-ascorbic acid in mind, we synthesized a series of novel l-ascorbic acid-conjugated pentacyclic triterpene derivatives (18-26, 29-31, 35-40 and 42-43). Moreover, we evaluated these novel compounds for their anti-influenza activities against A/WSN/33 virus in MDCK cells. Among all evaluated compounds, the 2,3-O,O-dibenzyl-6-deoxy-l-ascorbic acid-betulinic acid conjugate (30) showed the most significant anti-influenza activity with an EC50 of 8.7 μM, and no cytotoxic effects on MDCK cells were observed. Time-of-addition assay indicated that compound 30 acted at an early stage of the influenza life cycle. Further analyses revealed that influenza virus-induced hemagglutination of chicken red blood cells was inhibited by treatment of compound 30, and the interaction between the influenza hemagglutinin (HA) and compound 30 was determined by surface plasmon resonance (SPR) with a dissociation constant of KD = 3.76 μM. Finally, silico docking studies indicated that compound 30 and its derivative 31 were able to occupy the binding pocket of HA for sialic acid receptor. Collectively, these results suggested that l-ascorbic acid-conjugated pentacyclic triterpenes were promising anti-influenza entry inhibitors, and HA protein associated with viral entry was a promising drug target.

GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME

The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.