114682-33-6

Basic information

• Product Name: 2H-Pyran-3(6H)-one, 6-[(acetyloxy)methyl]-2-(1-methylethoxy)-, (2S,6S)-
• CAS NO: 114682-33-6
• Molecular Formula: C11H16O5
• Molecular Weight: 228.245
• Mol File: 114682-33-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-3(6H)-one, 6-[(acetyloxy)methyl]-2-(1-methylethoxy)-, (2S,6S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-3(6H)-one, 6-[(acetyloxy)methyl]-2-(1-methylethoxy)-, (2S,6S)-(114682-33-6)
• EPA Substance Registry System: 2H-Pyran-3(6H)-one, 6-[(acetyloxy)methyl]-2-(1-methylethoxy)-, (2S,6S)-(114682-33-6)

Safety Data

• Hazardous Substances Data: 114682-33-6(Hazardous Substances Data)

Upstream product

• 67-63-0 isopropyl alcohol 
• 14125-78-1 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 

Downstream Products

• 1449682-85-2 1-O-acetyl-6-O-benzyl-3,4-dideoxy-2-O-methyl-α-D-erythro-hexopyranose 
• 1449682-86-3 1-O-acetyl-6-O-benzyl-3,4-dideoxy-2-O-methyl-β-D-erythro-hexopyranose 
• 1101200-26-3 isopropyl 6-O-benzyl-3,4-dideoxy-2-O-methyl-α-D-erythro-hexopyranoside 
• 1153941-03-7 2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose 
• 1153941-07-1 2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-4-thio-α-D-erythro-hexopyranosid-2-ulose 
• 1032633-67-2 2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose 
• 1032633-69-4 2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose 
• 1032633-63-8 2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose 
• 1032633-74-1 2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5-tri-O-benzoyl-β-D-xylofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose 
• 208175-93-3 Toluene-4-sulfonic acid (2S,6S)-6-isopropoxy-5-oxo-tetrahydro-pyran-2-ylmethyl ester 
• 330825-87-1 2-propyl 3,4-dideoxy-2,6-di-O-tosyl-α-D-erythro-hexopyranoside 
• 330825-91-7 2-propyl 3,4-dideoxy-2,6-di-O-tosyl-α-D-erythro-hex-3-enopyranoside 
• 330825-94-0 2-propyl 2-azido-6-O-tosyl-2,3,4-trideoxy-α-D-thero-hex-3-enopyranoside 

Relevant articles and documents

Convenient Synthesis of Chiral Pyranones from Carbohydrates

2-Acyloxyglycals (2-O-acyl-1,5-anhydrohex-1-enitols) having a D-arabino configuration (1a, b) react highly stereoselectively with alcohols in the presence of a stoichiometric amount of tin(IV) chloride at O-5 deg C to (2S,6S)-6-acyloxymethyl-2-alkoxy-2H-pyran-3(6H)-ones 2 together with furaldehyde by-products 3.In the case of 2-acyloxyglycals having a D-lyxo (1c, d) or an L-lyxo (4) configuration, reaction occurs readily at -20 deg C to form the desired pyranones 2 or 5 without the formation of furaldehydes.All reactions showed high stereoselectivity for α-anomersin the formation of the acetal linkage, except the reaction of the tri-O-benzoyl derivative 1d with methanol.The method reported allows the synthesis of chiral pyranones in higher yield and by a shorter route than the previously reported methods.