215510-13-7

Basic information

• Product Name: 1-(β-D-glucopyranosyl)propan-2-one
• Synonyms: 1-(β-D-glucopyranosyl)propan-2-one
• CAS NO: 215510-13-7
• Molecular Weight: 220.222
• Mol File: 215510-13-7.mol

Chemical Properties

• CAS DataBase Reference: 1-(β-D-glucopyranosyl)propan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(β-D-glucopyranosyl)propan-2-one(215510-13-7)
• EPA Substance Registry System: 1-(β-D-glucopyranosyl)propan-2-one(215510-13-7)

Safety Data

• Hazardous Substances Data: 215510-13-7(Hazardous Substances Data)

Upstream product

• 2280-44-6 D-Glucose 
• 93-91-4 1-phenylbutan-1,3-dione 
• 57-48-7 D-Fructose 
• 123-54-6 acetylacetone 

Downstream Products

• 120520-81-2 4,8-anhydro-5,6,7,9-tetra-O-benzyl-1,3-dideoxy-D-glycero-D-gulo-non-2-ulose 
• 1173597-04-0 (E)-4-(3-hydroxy-4-methoxyphenyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1173597-05-1 (E)-4-[4-(benzyloxy)-3-methoxyphenyl]-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1173597-12-0 (E)-4-(3-bromophenyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1173597-14-2 (E)-4-[3-(trifluoromethyl)phenyl]-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1173597-08-4 (E)-4-p-tolyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1173597-11-9 (E)-4-(4-fluorophenyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1164131-44-5 (E)-4-(4-methoxyphenyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1173597-46-0 C₂₂H₂₉NO₈ 
• 1173597-01-7 (E)-4-(2-methoxyphenyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1173597-33-5 (E)-4-[4-(dimethylamino)phenyl]-1-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]but-3-en-2-one 
• 1173597-48-2 C₂₃H₃₂N₂O₇ 
• 1259413-52-9 C₂₅H₄₈N₂O₆ 
• 1268482-87-6 4-ethyl-5-heptyl-2-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)cyclohex-2-enone 

Relevant articles and documents

A 2-C-fructosyl-propanone locked in a 2,7-dioxabicyclo[3.2.1]octane framework

Condensation of D-fructose with pentane-2,4-dione in mildly alkaline aqueous solution generates a novel sugar-based scaffold: a 2-C-fructosyl-propanone compressed by formation of a cycloacetal into a 2,7-dioxabicyclo[3.2.1]octane framework.

C-glycosides by aqueous condensation of β-dicarbonyl compounds with unprotected sugars

Condensation of 1,3-diketones with unprotected aldoses in water, under mildly alkaline conditions, provides a convenient and effective route to C-glycosidic ketones in high yields. Reactions usually proceed with high β-'anomeric' stereoselectivity because product composition is determined by thermodynamic control. Mechanistically, the condensation follows a typical Knoevenagel scheme, after which an intramolecular oxa-Michael cyclization determines C-glycoside configuration by following an exo- or endo-trig pathway. With open-chain 1,3-diketones, an ensuing retro-Claisen fragmentation occurs to furnish simple glycosyl monoketones. The C-glycosides then slowly further dehydrate under the reaction conditions to give 2,5-disubstituted furans.