BIOMAT Database Logo BIOMAT Database Logo

Selective pivaloylation and diphenylacetylation of cyclomalto-oligosaccharides. 1994

F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Spain.

Regioselective acylation of cyclomalto-oligosaccharides was achieved using pivaloyl and diphenylacetyl chlorides. The reaction of cyclomaltohexaose (1) with pivaloyl chloride gave the hexakis(2,6-di-O-pivaloyl) derivative 19 in 66% yield. Similar reaction with cyclomalto-heptaose (2) led to the octakis(2I,6I,6II,6III,6IV,6V,6VI ,6VII-O-pivaloyl) 26 and the 17 heptakis(6-O-pivaloyl) derivatives in 34 and 26% yields, respectively. The octakis(6-O-pivaloyl) derivative 18 was the only compound isolated (72%) in the reaction of pivaloyl chloride with cyclomalto-octaose (3). Diphenylacetylation of 1-3 gave the symmetrical (20-22) and the non-symmetrical (27-29) per(6-O-diphenylacetyl) esters as major and minor products, respectively.

UI MeSH Term Description Entries
D008969 Molecular Sequence Data Descriptions of specific amino acid, carbohydrate, or nucleotide sequences which have appeared in the published literature and/or are deposited in and maintained by databanks such as GENBANK, European Molecular Biology Laboratory (EMBL), National Biomedical Research Foundation (NBRF), or other sequence repositories. Sequence Data, Molecular,Molecular Sequencing Data,Data, Molecular Sequence,Data, Molecular Sequencing,Sequencing Data, Molecular
D009844 Oligosaccharides Carbohydrates consisting of between two (DISACCHARIDES) and ten MONOSACCHARIDES connected by either an alpha- or beta-glycosidic link. They are found throughout nature in both the free and bound form. Oligosaccharide
D010421 Pentanoic Acids Straight-chain CARBOXYLIC ACIDS with the general formula C5H10O2. Acids, Pentanoic
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D003505 Cyclodextrins A homologous group of cyclic GLUCANS consisting of alpha-1,4 bound glucose units obtained by the action of cyclodextrin glucanotransferase on starch or similar substrates. The enzyme is produced by certain species of Bacillus. Cyclodextrins form inclusion complexes with a wide variety of substances. Cycloamylose,Cyclodextrin,Cyclodextrin Derivatives,Cyclomaltooligosaccharides,Derivatives, Cyclodextrin
D004158 Diphenylacetic Acids Monocarboxylic acid derivatives of acetic acids, where the methyl hydrogens have been replaced by two phenyl groups. Acids, Diphenylacetic
D000107 Acetylation Formation of an acetyl derivative. (Stedman, 25th ed) Acetylations
D047391 alpha-Cyclodextrins Cyclic GLUCANS consisting of six (6) glucopyranose units linked by 1,4-glycosidic bonds. alpha Cyclodextrins

Related Publications

F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Synthesis of branched cyclomalto-oligosaccharides using Pseudomonas isoamylase.
October 1986, Carbohydrate research,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Complexation of single- and double-chain surfactants by cyclomalto-oligosaccharides.
October 1989, Carbohydrate research,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
In vitro action of human and porcine alpha-amylases on cyclomalto-oligosaccharides.
September 1990, Carbohydrate research,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
13C-N.M.R. spectra of cyclomalto-oligosaccharides (cyclodextrins), their derivatives, and complexes with azo dyes.
June 1990, Carbohydrate research,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Isolation and characterization of novel heterogeneous branched cyclomalto-oligosaccharides (cyclodextrins) produced by transgalactosylation with alpha-galactosidase from coffee bean.
November 1995, Carbohydrate research,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Preparation, isolation, and characterization of novel heterogeneous branched cyclomalto-oligosaccharides having beta-D-galactosyl residue(s) on the side chain.
January 1993, Carbohydrate research,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Alkylation of cyclomalto-oligosaccharides (cyclodextrins) with dialkyl sulfate-barium hydroxide: heterogeneity of products and the marked effect of the size of the macrocycle.
October 1989, Carbohydrate research,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Post-source decay fragment spectra of cyclomalto-octaose and branched cyclomalto-hexaose by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
January 1996, Rapid communications in mass spectrometry : RCM,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Towards one-pot selective synthesis of cyclic oligosaccharides.
January 2022, Advances in carbohydrate chemistry and biochemistry,
F Santoyo-González, and J Isac-García, and A Vargas-Berenguel, and R Robles-Díaz, and F G Calvo-Flores
Distribution of substituents in O-(2-hydroxypropyl) derivatives of cyclomalto-oligosaccharides (cyclodextrins: influence of increasing substitution of the base used in the preparation, and of macrocyclic size.
January 1992, Carbohydrate research,
Copied contents to your clipboard!