6893-67-0

Basic information

• Product Name: 1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose
• Synonyms: 1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose
• CAS NO: 6893-67-0
• Molecular Weight: 398.412
• Mol File: 6893-67-0.mol

Chemical Properties

• CAS DataBase Reference: 1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose(6893-67-0)
• EPA Substance Registry System: 1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose(6893-67-0)

Safety Data

• Hazardous Substances Data: 6893-67-0(Hazardous Substances Data)

Upstream product

• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 532-20-7 D-xylofuranose 
• 98-88-4 benzoyl chloride 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 

Downstream Products

• 85026-60-4 (3R,4S,5R)-4-(benzoyloxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate 
• 83434-58-6 Di-O-benzoyl-3,5 di-O-acetyl-1,2 α-D-xylofurannose 
• 95530-07-7 1,2-di-O-acetyl-3,5-di-O-benzoyl-β-D-xylofuranose 
• 4105-29-7 [(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate 
• 191538-87-1 C₁₉H₁₆O₅ 
• 219989-60-3 Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester 
• 219989-63-6 C₂₃H₁₉FIN₃O₆ 
• 134379-77-4 β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine 
• 1028945-04-1 C₂₆H₂₈O₁₀ 
• 1202373-19-0 2-O-(2-acetoxyisopropyl)-1-O-acetyl-3,5-di-O-benzoyl-β-D-xylofuranoside 

Relevant articles and documents

3-(Dimethylamino)-1-propylamine: A cheap and versatile reagent for removal of byproducts in carbohydrate chemistry

Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.

2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: Synthesis and in vitro antitumour activity

Tiazofurin analogues bearing a 5-hydroxymethyl-2-methyl-tetrahydrofuro[2,3- d][1,3]dioxol-6-ol moiety as a sugar mimic (2 and 3), and two novel thiazole-based acyclo-C-nucleosides 4 and 16 have been synthesized in multistep sequences starting from d-xylose (compounds 2 and 3) or from d-arabinose (compounds 4 and 16). All synthesized analogues showed potent in vitro antitumour activities against a panel of human tumour cell lines. Flow cytometry data suggest that cytotoxic effects of analogues 2-4 and 16 in the culture of K562 cells might be mediated by apoptosis. It was also found that these analogues induced changes in cell cycle distribution of K562 cells. Results of western blot analysis (upregulation of Bax and downregulation of Bcl-2, activation of caspase-3 and the presence of a PARP cleavage product) suggest that tiazofurin mimics (2-4 and 16) in K562 cells induced apoptosis in a caspase-dependent way.

Synthesis and in vitro antitumour screening of 2-(β-d-xylofuranosyl) thiazole-4-carboxamide and two novel tiazofurin analogues with substituted tetrahydrofurodioxol moiety as a sugar mimic

2-(β-d-xylofuranosyl)thiazole-4-carboxamide (2) and two new tiazofurin analogues with 5-hydroxymethyl-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol moiety as a sugar mimic (27 and 28) have been synthesized and evaluated for their in vitro antitumour activity against a panel of human tumour cell lines (K562, HL 60, Jurkat, Raji and HeLa). In contrast to previous literature reports, a metabolic MTT assay revealed remarkable cytotoxicity of 2 against K562 (IC50 = 0.15 μM) and HL-60 (IC50 = 0.13 μM) cells. Flow cytometry data suggest that cytotoxic effects of analogue 2 in the culture of K562 cells might be mediated by apoptosis, in opposite to tiazofurin, which did not induce apoptosis of K562 cells after 24 h, thus suggesting a different mechanism of action. All three analogues 2, 27 and 28 were also active against Jurkat, Raji and HeLa cells, with IC50 values in the range from 0.06 to 5.61 μM, but were completely inactive against the normal foetal lung fibroblasts (MRC-5).

Synthesis and comparative evaluation of two antiviral agents: β-L- Fd4C and β-D-Fd4C

The synthesis of β-D-Fd4C was achieved in a stereoselective fashion from D-xylose. The antiviral activity and cytotoxicity of β-D-Fd4C was compared with that of β-L-Fd4C and 3TC (Lamivudine). Of the three agents compared, β-L-Fd4C was found to be the most potent antiviral agent.