One-Pot Stereospecific\nSynthesis of 1,4-Oligosaccharides\nby Glycal-Derived Vinyl Epoxides Assembly

Recently, naturally\noccurring linear 1,4-glycans have attracted\nremarkable attention for their activity in cancer and neurodegenerative\ndisease treatment. Classical chemical synthetic strategies for linear\n1,4-oligosaccharides are considerably time-consuming due to orthogonal\nprotection/deprotection, the introduction of leaving groups, and various\nforms of activation of the glycosylation reaction. Herein, we present\na new one-pot microwave-activated reiterative assembly of glycal-derived\nvinyl epoxides in an uncatalyzed substrate-dependent stereospecific\nprocess for the preparation of both β-1,4-d-Gulo and\nα-1,4-d-Manno oligosaccharides.

Publication Details

Journal
Figshare
Published
2024-10-31
DOI
https://doi.org/10.1021/acsomega.4c05247.s001
Primary Topic
Genetic Mapping and Diversity in Plants and Animals
Type
article
Field-Weighted Citation Impact
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article

One-Pot Stereospecific\nSynthesis of 1,4-Oligosaccharides\nby Glycal-Derived Vinyl Epoxides Assembly

Figshare
Genetic Mapping and Diversity in Plants and Animals
article

One-Pot Stereospecific\nSynthesis of 1,4-Oligosaccharides\nby Glycal-Derived Vinyl Epoxides Assembly

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Abstract

Recently, naturally\noccurring linear 1,4-glycans have attracted\nremarkable attention for their activity in cancer and neurodegenerative\ndisease treatment. Classical chemical synthetic strategies for linear\n1,4-oligosaccharides are considerably time-consuming due to orthogonal\nprotection/deprotection, the introduction of leaving groups, and various\nforms of activation of the glycosylation reaction. Herein, we present\na new one-pot microwave-activated reiterative assembly of glycal-derived\nvinyl epoxides in an uncatalyzed substrate-dependent stereospecific\nprocess for the preparation of both β-1,4-d-Gulo and\nα-1,4-d-Manno oligosaccharides.

Figshare
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Genetic Mapping and Diversity in Plants and Animals
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One-Pot Stereospecific\nSynthesis of 1,4-Oligosaccharides\nby Glycal-Derived Vinyl Epoxides Assembly · Figshare (2024) | TGRS Research Map | TGRS