Glycosyl esters of amino acids : Part IV. Synthesis of 1-O-(acylaminoacyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranoses by the imidazole-promoted active ester and dicyclohexylcarbodiimide methods

doi:10.1016/S0008-6215(00)81275-6

Paper

DOI: 10.1016/S0008-6215(00)81275-6

Glycosyl esters of amino acids : Part IV. Synthesis of 1-O-(acylaminoacyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranoses by the imidazole-promoted active ester and dicyclohexylcarbodiimide methods

Published May 1, 1972 · D. Keglević, A. Kornhauser, S. Valenteković

Carbohydrate Research

Q2 SJR score

Citations

Influential Citations

Full textSemantic Scholar

Abstract

Abstract hidden due to publisher request; this does not indicate any issues with the research. Click the full text link above to read the abstract and view the original source.

Study Snapshot

High yields of 1-O-(acylaminoacyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranoses were achieved using the imidazole-promoted active ester and dicyclohexylcarbodiimide methods, with

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Full text analysis coming soon...

References

DOI: 10.1016/S0008-6215(00)80600-X

Glycosyl esters of amino acids : Part II. Synthesis of 2,3,4,6-tetra-O-acetyl-1-O-(2-acyl-D- and L-aminoacyl)-β-D-glucopyranoses. Studies of the racemization of the amino acid moiety

Acetylated 1-O-(2-acyl-D- and L-aminoacyl)--D-glucopyranoses can be synthesized with 80-85% retention of configuration, while racemization occurs with acetyl as the N-protecting group in method (a).

1970·7citations·A. Kornhauser et al.·Carbohydrate Research

Carbohydrate Research

DOI: 10.1016/S0008-6215(00)80583-2

Glycosyl esters of amino acids : Part I. Synthesis of 1-O-(2-acetamidoacyl)-2,3,4,6-tetra-O-acetyl-β-d-glucopyranoses

The silver salt and dicyclohexylcarbodiimide method successfully synthesized crystalline 1-O-(2-acetamidoacyl)-2,3,4,6-tetra-O-acetyl--d-glucopyranoses, which can be deacety

1969·12citations·A. Kornhauser et al.·Carbohydrate Research

Carbohydrate Research

DOI: 10.1002/JPS.2600580815

Sequential polypeptides: Synthesis of N-protected, C-activiated peptides from C-terminal residues of amino acids.

This modified mixed anhydride method effectively synthesizes N-protected, C-activated peptide units for sequential polypeptides, limiting racemization during the process.

1969·13citations·A. Kapoor et al.·Journal of pharmaceutical sciences

Journal of pharmaceutical sciences

DOI: 10.1071/CH9681639

Depsipeptide synthesis by accelerated active ester coupling

Accelerated active ester coupling effectively synthesizes depsipeptide derivatives in high yield, with pentamethylbenzyl being a key carboxyl-protecting group.

1968·17citations·F. Stewart·Australian Journal of Chemistry

Australian Journal of Chemistry

Citations

DOI: 10.1111/J.1399-3011.1988.TB00908.X

Synthesis and biological activity of [Leu5]enkephalin derivatives containing D-glucose.

[Leu5]enkephalin derivatives with D-glucose show full opioid activity and are delta-receptor selective, with the most potent being 1-O conjugate 5.

2009·31citations·J. Horvat et al.·International journal of peptide and protein research

International journal of peptide and protein research

DOI: 10.1016/S0040-4020(97)01038-7

Zirconocene-catalyzed epoxy ester - ortho ester rearrangement: A new method for the protection of polyfunctionalized carboxylic acids and the asymmetric synthesis of ortho esters

Zirconocene-catalyzed epoxy ester - ortho ester rearrangement enables the efficient protection of polyfunctionalized carboxylic acids and the asymmetric synthesis of ortho esters.

1997·26citations·P. Wipf et al.·Tetrahedron

Tetrahedron

DOI: 10.1016/S0008-6215(00)90456-7

Synthesis and diazomethane-catalysed 1→2 acyl migration of the l-arabinosyl esters of N-acylamino acids

Diazomethane-catalyzed 12 acyl migration of l-arabinosyl esters of N-acylamino acids leads to the formation of 1,3,4- and 1,3,5-tri-O-acetyl-2-O-(N-tert-

1985·2citations·J. Horvat et al.·Carbohydrate Research

Carbohydrate Research

DOI: 10.1080/07328308208085079

Synthesis and Reactions of 2,3,4,6-Tetra-O-Acetyl-1-S-(N-Acylaminoacyl)-1-Thio-β-D-Glucopyranoses

Acetylated 1-thio--D-glucopyranosyl esters of N-protected amino acids can be prepared in high yields, with potential for S-O and S-N migrations in reactions with alcohols and amines.

1983·6citations·S. Tomić et al.·Journal of Carbohydrate Chemistry

Journal of Carbohydrate Chemistry

DOI: 10.1016/S0008-6215(00)81893-5

Peptide bond formation by intermolecular aminolysis of d-glucopyranosyl esters of amino acids

Intermolecular aminolysis of d-glucopyranosyl esters of amino acids can form peptide bonds, with reactivity influenced by the amino acid nucleophile, aglycon side-chain group, and the anomeric configuration of the d-glucopyranos

1982·7citations·Š. Horvat et al.·Carbohydrate Research

Carbohydrate Research

DOI: 10.1246/BCSJ.51.2401

A Convenient Procedure for Esterification of Carboxylic Acids

This simple reaction provides a general method for esterifying various carboxylic acids, yielding esters in good yields in various conditions.

1978·127citations·N. Ono et al.·Bulletin of the Chemical Society of Japan

Bulletin of the Chemical Society of Japan

DOI: 10.1016/0005-2736(76)90510-1

1-O-acyl derivatives of glucose as non-penetrating inhibitors of glucose transport by hamster small intestine in vitro.

1-O-acyl derivatives of glucose are potent inhibitors of glucose transport in the hamster small intestine, but do not pass through it in vitro.

1976·2citations·K. Ramaswamy et al.·Biochimica et biophysica acta

Biochimica et biophysica acta