Selective 4,6-O-benzylidene formation of methyl α-D-mannopyranoside using 2,6-dimethylbenzaldehyde.

doi:10.1016/j.carres.2014.02.024

Paper

Selective 4,6-O-benzylidene formation of methyl α-D-mannopyranoside using 2,6-dimethylbenzaldehyde.

Published Jun 4, 2014 · L. Liotta, Jennifer F Chalmers, Jessica N Falco Marshall

Carbohydrate research

Q2 SJR score

3

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0

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Abstract

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Study Snapshot

Using 2,6-dimethylbenzaldehyde instead of benzaldehyde effectively restores selectivity for 4,6-O-benzylidene formation in methyl -D-mannopyranoside, making it a useful tool in chemical synthesis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Selective 4,6-O-benzylidene formation of methyl α-D-mannopyranoside using 2,6-dimethylbenzaldehyde.

References

Organocatalysis for the Acid‐Free O‐Arylidenation of Carbohydrates

Organocatalysis allows for the regioselective 4,6-O-arylidenation of carbohydrates, resulting in regioselectively 4,6-O-arylidenated derivatives and diarylidenated derivatives.

Regioselective and stereoselective benzylidene installation and one-pot protection of D-mannose.

One-pot procedures for preparing fully protected and 2-, 3-, 4-, and 6-alcohol derivatives of D-mannose enable efficient and time-saving sugar building block preparation for oligosaccharide syntheses.

Studies related to Norway spruce galactoglucomannans: chemical synthesis, conformation analysis, NMR spectroscopic characterization, and molecular recognition of model compounds.

This study successfully synthesized and studied distinct fragments of Norway spruce galactoglucomannan, revealing potential applications in pulp and paper, food, and medical industries.

2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks.

TCT-mediated one-pot sequential functionalisation of glycosides produces orthogonally protected monosaccharide building blocks with high regioselectivity, broad substrate use, functional group tolerance, mild reaction conditions, and wide application range.

TMDS as a Dual‐Purpose Reductant in the Regioselective Ring Cleavage of Hexopyranosyl Acetals to Ethers

TMDS is a highly regioselective reductant for the synthesis of carbohydrate-based surfactants by cleaving hexopyranosyl acetals to ethers.

Citations

Efficient synthesis for each of the eight stereoisomers of the iminosugars lentiginosine and 1,4-dideoxy-1,4-imino-D-arabinitol (DAB).

This study demonstrates efficient, diastereoselective synthesis of the iminosugars lentiginosine and 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) with high yields, using commercially available sugars.

Six New Phenolic Glycosides from the Seeds of Moringa oleifera Lam. and Their α-Glucosidase Inhibitory Activity

Six new phenolic glycosides from Moringa oleifera seeds show promising inhibitory activities against -glucosidase, with compound 16 showing better activity than acarbose.