The synthesis of .ALPHA.-D-galactopyranosyl and .ALPHA.-D-mannopyranosyl 2-amino-2-deoxy-.ALPHA.-D-glucopyranosides and the conformation of their glycoside linkage.

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概要

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• A new analog of trehalosamine, α-D-galactopyranosyl 2-amino-2-deoxy-α-D-glucopyranoside, was synthesized by the glycosylation of 2,3,4,6-tetra-<I>O</I>-(<I>p</I>-chlorobenzyl)-α-D-galactopyranose with 3,4,6-tri-<I>O</I>-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide, using silver perchlorate and tribenzylamine in benzene, followed by chromatographic separation and the subsequent removal of the protecting groups. Similarly, α-D-mannopyranosyl 2-amino-2-deoxy-α-D-glucopyranoside was synthesized. The conformation of the glycoside linkage of these α,α-disaccharides is discussed in relation to the <SUP>13</SUP>C chemical shifts of their anomeric carbons.

• 公益社団法人 日本化学会の論文

著者

• Zen Shonosuke

  School Of Pharmaceutical Sciences Kitasato University

• Koto Shinkiti

  School Of Pharmaceutical Sciences Kitasato University

• Inada Shigeru

  School of Pharmaceutical Sciences, Kitasato University

関連論文

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• Glycosylation Using 2-Azido-3,4,6-tri-ο-benzyl-2-deoxy-D-glucose,-galactose, and -mannose with the Aid of ρ-Nitrobenzenesulfonyl Chloride-Silver Trifluoromethanesulfonate-Triethylamine System
• Synthesis of Glucose-Containing Linear Oligosaccharides Having α(1→4) and α(1→6) Linkages Using Stereoselective Dehydrative Glycosylation
• Synthesis and Utility of 2-(Benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl Bromide as a Novel α-D-Talosaminide Building Block
• A Practical Synthesis of Mannosaminyl-β(1→4)-glucosyl-α(1→2)-rhamnose, the Trisaccharide Repeating Unit of a Streptococcus pneumoniae Capsular Polysaccharide
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• Glycosylation Using Hemiacetal Sugar Derivatives : Synthesis of O-α-D-Rhamnosyl-(1→3)-O-α-D-rhamnosyl-(1→2)-D-rhamnose and O-α-D-Tyvelosyl-(1→3)-O-α-D-mannosyl-(1→4)-L-rhamnose
• A Novel, Readily Accessible Lactosaminyl Donor : N-Trichloroethoxycarbonyl-hexa-0-benzoyl-β-D-lactosaminyl Fluoride :
• Syntheses of O-β-D-Mannosyl-(1→4)-O-α-D-mannosyl-(1→3)-L-rhamnose and O-(2-Acetamido-2-deoxy-β-D-mannosyl)-(1→4)-O-α-D-galactosyl-(1→4)-D-galactose via In-situ-activating Glycosylation Using 2-O-Acetyl-3, 4, 6-tri-O-benzyl-D-glucose
• Stereoselective Syntheses of α-Glucuronides Using Dehydrative Glycosylation
• Synthesis of Methyl O -IX- D Mannosyl (1→4)-[(3-O-methyl-α-D-mannosyl)-(1→4) ]_n 3-O methyl-α-D-mannosides (n=O, 1, and 2) via Dehydrative Glycosylation
• Dehydrative Glycosylation by Diethylaminosulfur Trifluoride (DAST)-Tin(II) Trifluoromethanesulfonate-Tetrabutylammonium Perchlorate-Triethylamine System
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• Syntheses of Isomaltose, Isomaltotetraose, and Isomaltooctaose
• A study of the rapid anomerization of poly-O-benzyl-.BETA.-D-glucopyranosides with titanium tetrachloride.
• A stereoselective one-stage .ALPHA.-glucosylation with 2,3,4,6-tetra-O-benzyl-.ALPHA.-D-glucopyranose and a mixture of methanesulfonic acid, cobalt(II) bromide, and tetraethylammonium perchlorate.
• The direct synthesis of methyl 2,4-di-O-benzyl-.ALPHA.-D-xylopyranoside by the regiospecific benzylation of methyl .ALPHA.-D-xylopyranoside.
• Synthesis of O-.BETA.-D-glucopyranosyl-(1.RAR.2)-O-.BETA.-D-glucopyranosyl-(1.RAR.6)-D-glucopyranose; Dehydrative .BETA.-D-glucosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose.
• The synthesis of .ALPHA.-D-galactopyranosyl and .ALPHA.-D-mannopyranosyl 2-amino-2-deoxy-.ALPHA.-D-glucopyranosides and the conformation of their glycoside linkage.
• .ALPHA.-D-glucosylation by 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose using trimethylsilyl triflate and pyridine. Synthesis of .ALPHA.-maltosyl and .ALPHA.-isomaltosyl .ALPHA.-D-glucosides.
• Partial benzylation of methyl .ALPHA.- and .BETA.-D-galactopyranosides.
• Stereoselective synthesis of mixed acetal glycosides by reaction of tri-O-acetyl-N-(2,4-dinitrophenyl)-.ALPHA.-D-glucosaminyl bromide with alcohol in acetone.
• A through-process for the preparation of methyl per-O-acetyl 1-thio-glycosides from aldoses.
• Synthesis of Anomeric Methyl 6-O-(L-Mycarosyl)-β-D-glucosaminides and 4-O-(L-Mycarosyl)-β-D-mycaminosides
• The Synthesis of Methyl 2,4,6-Tri-O-benzyl-α-D-glucopyranoside
• Partially benzylated derivatives of 6-deoxy-D-glucose.
• .ALPHA.-Glucosylation of phenols with tetra-O-benzyl-.ALPHA.-D-glucose.
• The stereoselective dehydrative .ALPHA.-glucosylation using 6-O-acetyl- and 6-O-p-nitrobenzoyl-2,3,4-tri-O-benzyl-D-glucopyranoses.
• Synthesis of 4-Substituted Isoxazole-3,5-dicarboxylic Acids from 2-Substituted-1,3-dinitroglutarates and the Reaction Mechanism therefrom
• Glucosidation of tetra-O-benzyl-.ALPHA.-D-glucose with chlorosilane and silver sulfonate.
• Preparation of 2,3,4,6-tetra-O-benzyl-D-mannose.
• The Synthesis of Purine Nucleosides of L-Mycarose and L-Cladinose
• Stereoselective .ALPHA.-glucosylation with tetra-O-benzyl-.ALPHA.-D-glucose and a mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and a molecular sieve. A synthesis of 3,6-di-O-(.ALPHA.-D-glucopyranosyl)-D-glucose.
• The Synthesis of 3-Amino-3-deoxy-D-allose and Related Substances
• 2-methoxyethyl group for protection of reducing hydroxyl group of aldose.
• Studies on 5-8 fused ring compounds. V. The conformations of eight-membered rings in 5-8-5 fused ring compounds and their cis-trans isomerization.
• The glucosylation of several alcohols with tetra-O-benzyl-.ALPHA.-D-glucopyranose and a mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine.
• A facile synthesis of anomeric methyl DL-tolyposaminides, methyl DL-forosaminides, and related substances.

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