74580-97-5

Basic information

• Product Name: O⁵-acetyl-O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-α-D-xylofuranose
• CAS NO: 74580-97-5
• Molecular Weight: 386.423
• Mol File: 74580-97-5.mol

Chemical Properties

• CAS DataBase Reference: O⁵-acetyl-O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-α-D-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: O⁵-acetyl-O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-α-D-xylofuranose(74580-97-5)
• EPA Substance Registry System: O⁵-acetyl-O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-α-D-xylofuranose(74580-97-5)

Safety Data

• Hazardous Substances Data: 74580-97-5(Hazardous Substances Data)

Upstream product

• 171720-97-1 (3aS,5S,6R,6aS)-2,2-dimethyl-5-((tosyloxy)methyl)tetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 127-08-2 potassium acetate 
• 108-24-7 acetic anhydride 
• 80244-96-8 5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 16713-88-5 1,2-O-isopropylidene-3-O-tosyl-α-D-xylopentofuranose 
• 74580-94-2 1,2-O-isopropylidene-5-O-(methoxycarbonyl)-3-O-tosyl-α-D-xylofuranose 
• 114861-22-2 1,2-O-isopropylidene-α-L-xylofuranose 

Relevant articles and documents

Nucleosides. 116. 1-(β-D-Xylofuranosyl)-5-fluorocytosines with a Leaving Group on the 3' Position. Potential Double-Barreled Masked Precursors of Anticancer Nucleosides

Syntheses of five pairs of cytosine and 5-fluorocytosine xylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, I, OMs, or OTs are described.Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine.Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thymidine but not by deoxycytidine.These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.