14125-78-1

Basic information

• Product Name: 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol
• Synonyms: 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol
• CAS NO: 14125-78-1
• Molecular Weight: 330.292
• Mol File: 14125-78-1.mol

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol(14125-78-1)
• EPA Substance Registry System: 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol(14125-78-1)

Safety Data

• Hazardous Substances Data: 14125-78-1(Hazardous Substances Data)

Upstream product

• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 122359-37-9 (-)-(5R,6R)-3,5-Bis(acetoxy)-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-one 
• 122359-45-9 Acetic acid (2R,5R,6R)-5-acetoxy-6-acetoxymethyl-2-(3-chloro-benzoylperoxy)-5,6-dihydro-2H-pyran-3-yl ester 
• 10551-58-3 5-acetoxymethyl-2-furaldehyde 
• 114682-33-6 2-isopropyl 6-O-acetyl-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose 
• 71021-12-0 1,6-Di-O-acetyl-3,4-didesoxy-α-D-glycero-hex-3-enopyranos-2-ulose 
• 14125-89-4 1,2,4,6-Tetra-O-acetyl-3-desoxy-α-D-threo-hex-2-enopyranose 
• 82916-44-7 1,6-Di-O-acetyl-3,4-didesoxy-β-D-glycero-hex-3-enopyranos-2-ulose 
• 70532-55-7 1,2,4,6-Tetra-O-acetyl-3-desoxy-β-D-threo-hex-2-enopyranose 
• 463935-90-2 benzyl 6-O-acetyl-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose 
• 79292-20-9 Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(diisopropoxy-phosphorylmethyl)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 61332-59-0 (4aR,6S,7R,8R,8aR)-7,8-Dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester 
• 79292-19-6 (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol 
• 79292-18-5 (2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 79305-71-8 Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-chloromethyl-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Preparation of Unsaturated Carbohydrates by Ester Pyrolysis, II. - Thermal cis Eliminations from Completely Acetylated Aldopyranoses

The pentaacetates 1, 2, 7, and 9 of β-D-glucose, α-D-mannose, β-D-allose, and β-D-galactose and the tetraacetates 13 and 18 of β-D-xylose and β-D-ribose eliminate when dissolved in acetone at temperatures about 350 deg C in a flow apparatus within 0.5 - 1 min regioselectively and stereoselectively the 1-O-acetate group.The respective anomers with trans-bound hydrogen in position 2 do not give this reaction corresponding to the pericyclic elimination mechanism.In a subsequent sigmatropic rearrangement the primarily formed 2,3,4,6-tetra-O-acetyl-1,5-anhydro-hex-1-enitols 3 (from 1 or 2), 8, and 10 as well as the 2,3,4-tri-O-acetyl-1,5-anhydro-pent-1-enitols 14 and 19 yield the α- or β-triacetyl-3-deoxy-hex-2-enopyranoses 4 or 5, 12 and the α- or β-triacetyl-3-deoxy-pent-2-enopyranoses 15 or 16, respectively.These products partially anomerize, e.g. 12 gives 11. - By further rearrangement with subsequent acetic acid anhydride elimination 5 and 16 are transformed into the enones 6 and 17. - 1,2,4,6-Tetra-O-acetyl-3-deoxy-β-D-threo-hex-2-enopyranose (12) is described for the first time.The 0H5(D)conformations of 11 and 12 are established by 13C NMR data.