- Synthesis of 1,4-anhydro-d-fructose and 1,4-anhydro-d-tagatose
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1,4-Anhydro-d-fructose and 1,4-anhydro-d-tagatose were prepared from 1,2-O-isopropylidene-d-glucofuranose via the common intermediate 3,5,6-tri-O-benzyl-d-glucitol. The title compounds may be interesting anti-oxidants and feature activities akin to their natural pyranoid counterpart, 1,5-anhydro-d-fructose.
- Dekany, Gyula,Lundt, Inge,Steiner, Andreas J.,Stuetz, Arnold E.
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- Preparation of sugar-derived α-acetoxy-aldehydes
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A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).
- Jarosz,Kozlowska
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- Enantiospecific Synthesis of (2S,3S,5S)-2-Acetamido-2,4-dideoxyhexopyranose (N-Acetyl-4-deoxy-D-mannosamine) from D-Glucose
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A 14-step enantiospecific total synthesis (overall yield 6percent) of the title compound 1 from the known furanose 4 (derived from D-glucose) is described. Key Words: Carbohydrates, total synthesis of / Amino sugars / Mannosamine
- Mulzer, Johann,Seilz, Carsten,Reutter, Werner
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p. 957 - 960
(2007/10/02)
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