30694-66-7

Upstream product

• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 4627-30-9 1,2,3,4-tetra-O-acetyl-β-D-ribopyranose 

Downstream Products

• 866101-46-4 phenyl 2,4-di-O-acetyl-3-deoxy-1-thio-β-D-glycero-pent-2-enopyranoside 
• 1419313-64-6 (S)-4-methyl-N-(3-oxo-3,6-dihydro-2H-pyran-2-yl)benzenesulfonamide 
• 1419313-66-8 (R)-4-methyl-N-(3-oxo-3,6-dihydro-2H-pyran-2-yl)benzenesulfonamide 
• 1419313-76-0 C₁₈H₂₃NO₄S 
• 391928-90-8 (2S)-2-benzyloxy-2H-pyran-3-(6H)-one 
• 476487-90-8 (3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one 
• 581095-83-2 (3S,4aS,5R,8S,8aR)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-methano-1H-2-benzopyran-4(3H)-one 
• 476487-84-0 (3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-methano-1H-2-benzopyran-4(3H)-one 
• 1610827-43-4 menthyl 3,4-dideoxy-(1S)-pent-3-enopyranosid-2-ulose 
• 1610827-50-3 C₂₅H₃₆N₂O₅ 
• 1610827-49-0 C₃₂H₄₁NO₅ 
• 1610827-48-9 C₂₆H₃₇NO₅ 
• 1610827-46-7 C₂₆H₃₇NO₅ 
• 1610827-45-6 C₂₆H₃₇NO₅ 

Relevant academic research and scientific papers

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.