Facile Synthesis of a Branched Trisaccharide–The Repeating Unit of Antigen O2 Polymer using Orthoester Formation - Rearrangement Strategy

Wang, Wei; Kong, Fanzuo

doi:10.1080/07328309908543994

Cited by 6 publications

(1 citation statement)

References 9 publications

(4 reference statements)

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“…Compounds 18 , 19 , and 20 were white crystals enabling their separation and purification easily. The ortho ester 18 is a very important intermediate; modifications at both nonreducing and reducing ends will give a facile route to synthesis of complex oligosaccharides.…”

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Highly Regio- and Stereoselective Synthesis of Bioactive Oligosaccharides Using 1,2-O-Ethylidene-α-d-gluco- and -β-d-Mannopyranose as the Acceptors and Acetobromosugars as the Donors via Ortho Ester Intermediates

Wei

Kong

1999

J. Org. Chem.

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This paper presents a new, and effective method for highly regio- and stereoselective synthesis of oligosaccharides with 1,2-trans linkages using 1,2-O-ethylidenated gluco- and mannopyranose as the acceptors and simple acetobromosugars as the glycosyl donors through ortho ester formation−rearrangement strategy. Biologically important 3,6-branched oligosaccharides such as the phytoalexin elicitor hexasaccharide and ConA-binding 3,6-branched mannotriose were synthesized readily in high yields by the new method.

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confidence: 99%

Highly Regio- and Stereoselective Synthesis of Bioactive Oligosaccharides Using 1,2-O-Ethylidene-α-d-gluco- and -β-d-Mannopyranose as the Acceptors and Acetobromosugars as the Donors via Ortho Ester Intermediates

Wei

Kong

1999

J. Org. Chem.

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Other Methods of Glycosylation

Panza

Lay

2000

Carbohydrates in Chemistry and Biology

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Recent studies on reaction pathways and applications of sugar orthoesters in synthesis of oligosaccharides

Kong

2007

Carbohydrate Research

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107

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Abstract-Formation of sugar-sugar orthoesters consisting of a fully acylated mono-or disaccharide donor and a partially protected mono-or disaccharide acceptor is regioselective, and rearrangement of the orthoesters via RO-(orthoester)C bond cleavage gives a dioxolenium ion intermediate leading to 1,2-trans glycosidic linkage. The activity order of hydroxyl groups in the partially protected mannose and glucose acceptors is 6-OH > 3-OH > 2-or 4-OH. The coupling reactions with acylated glycosyl trichloroacetimidates as the donors usually give orthoesters as the intermediates specially when the coupling is carried out at slowed rates, and this is successfully used in regio-and stereoselective syntheses of oligosaccharides. Mannose and rhamnose orthoesters readily undergo O-2-(orthoester)C bond breaking, and this is used for synthesis of a-(1!2)-linked oligosaccharides. (1!3)-Glucosylation is special since the rearrangement of its sugar orthoester intermediates can occur with either RO-(orthoester)C bond cleavage with formation of the dioxolenium ion leading to 1,2-trans linkage, or C-1-O-1 bond cleavage leading to 1,2-cis linkage, and this is dependent upon the structures of donor and acceptor that compose the orthoester.

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Facile Synthesis of a Branched Trisaccharide–The Repeating Unit of Antigen O2 Polymer using Orthoester Formation - Rearrangement Strategy

Abstract: The synthesis of a branched trisaccharide, the repeating unit of the antigen 02 polymer containing L-rhamnose, D-mannose, and L-xylose, was achieved using orthoester formation -rearrangement strategy.

Cited by 6 publications

References 9 publications

Highly Regio- and Stereoselective Synthesis of Bioactive Oligosaccharides Using 1,2-O-Ethylidene-α-d-gluco- and -β-d-Mannopyranose as the Acceptors and Acetobromosugars as the Donors via Ortho Ester Intermediates

Highly Regio- and Stereoselective Synthesis of Bioactive Oligosaccharides Using 1,2-O-Ethylidene-α-d-gluco- and -β-d-Mannopyranose as the Acceptors and Acetobromosugars as the Donors via Ortho Ester Intermediates

Other Methods of Glycosylation

Recent studies on reaction pathways and applications of sugar orthoesters in synthesis of oligosaccharides

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