17225-57-9

Basic information

• Product Name: 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexo-5-enofuranose
• CAS NO: 17225-57-9
• Molecular Weight: 228.245
• Mol File: 17225-57-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexo-5-enofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexo-5-enofuranose(17225-57-9)
• EPA Substance Registry System: 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexo-5-enofuranose(17225-57-9)

Safety Data

• Hazardous Substances Data: 17225-57-9(Hazardous Substances Data)

Upstream product

• 2946-02-3 1,2-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose O-acetate 

Downstream Products

• 24807-96-3 3-O-acetyl-1,2-O-isopropylidene-β-L-idofuranose 
• 24807-96-3 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 118226-57-6 Acetic acid (3aR,5S,6S,6aR)-2,2-dimethyl-5-[(R)-3-(2,4,6-trimethyl-phenyl)-4,5-dihydro-isoxazol-5-yl]-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 118332-58-4 Acetic acid (3aR,5S,6S,6aR)-2,2-dimethyl-5-[(S)-3-(2,4,6-trimethyl-phenyl)-4,5-dihydro-isoxazol-5-yl]-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Relevant articles and documents

Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: Synthesis of 5-thioglucose

The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2, when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other hand, thermolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.