Oxazoline synthesis of 1,2-trans-2-acetamido-2-deoxyglycosides. Glycosylation of secondary hydroxyl groups in partially protected saccharides

doi:10.1016/S0008-6215(00)80289-X

Paper

Oxazoline synthesis of 1,2-trans-2-acetamido-2-deoxyglycosides. Glycosylation of secondary hydroxyl groups in partially protected saccharides

Published Oct 1, 1970 · S. E. Zurabyan, T. Antonenko, A. Khorlin

Carbohydrate Research

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42

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Abstract

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Study Snapshot

The oxazoline method effectively synthesizes 1,2-trans-2-acetamido-2-deoxyglycosides, enabling the synthesis of various glycosylated partially protected saccharides with free secondary hydroxyl groups.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Oxazoline synthesis of 1,2-trans-2-acetamido-2-deoxyglycosides. Glycosylation of secondary hydroxyl groups in partially protected saccharides

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References

Oxazoline synthesis of 1,2-trans-2-acetamido-2-deoxyglycosides

Oxazolines can effectively synthesize 1,2-trans-2-acetamido-2-deoxyglycosides in up to 50% yields with p-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy--D -

Lysozyme substrates. Synthesis of p-nitrophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside and its β-D-(1 → 6) isomer

Egg-white lysozyme can hydrolyze compound V, but not XI and p-nitrophenyl 2-acetamido-2-deoxy--D-glucopyranoside (VI), suggesting bacterial resistance mechanisms.

The synthesis of a 2-amino-2-deoxy-d-glucosyl-muramic acid disaccharide: 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucopyranosyl)-i,4-di-O-acetyl-2-deoxy- 3-O-[d-i-(methyl carboxylate)ethyl]- α-d-glucopyranose

A crystalline disaccharide derivative containing β-(1 → 6)-linked 2-amino-2-deoxy-d-glucose and muramic acid was successfully synthesized, with a 6% yield.

Citations

Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines

The development of DMC-mediated oxazoline formation in water simplifies synthetic strategies, allowing access to larger and more complex N-glycan structures from natural sources.

Glycosylation with 2-Acetamido-2-deoxyglycosyl Donors at a Low Temperature: Scope of the Non-Oxazoline Method.

The non-oxyazoline method allows for the direct construction of 1,2-trans--linked 2-acetamido-2-deoxyglycosides at low temperatures, with potential for use as attractive alternatives to phosphite-based glycosylations.

Oxazolines: Their Synthesis and Biological Activity

Oxazolines play a significant role in various industries, with their core structure being crucial for biologically active compounds with diverse biological activities.

Multi‐Gram Synthesis of a Hyaluronic Acid Subunit and Synthesis of Fully Protected Oligomers

Hyaluronic acid oligomers can be synthesized in large quantities using a key building block, allyl, and a trichloroacetimidate method.

Facile approach to 2-acetamido-2-deoxy-beta-D-glucopyranosides via a furanosyl oxazoline.

This study presents a convenient and efficient method for preparing unprotected beta-glucopyranosides from N-acetyl-D-glucosamine by reacting various alcohols with a reactive furanosyl oxazoline under acidic conditions.

Copper(II)-Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β-Glycosides ofN-Acetylglucosamine

Copper(II)-mediated activation of sugar oxazolines allows for the mild and efficient synthesis of -glycosides of N-acetylglucosamine in 36-92% yield.