Biomaterial Database

The synthesis of allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside and of chitobiose derivatives by the oxazoline procedure. 1977

C D Warren, and R W Jeanloz

Controlled, partial benzylation of allyl 2-acetamido-3-O-benzyl-2-deoxy-alpha-D-glucopyranoside gave a mixture of the 3,4-di-, 3,6-di- (15), and 3,4,6-tri-O-benzyl derivatives, the major product being 15. Condensation of 15 with 2-methyl-(3,4,6-tri-O-acetul-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-d]-2-oxazoline gave a disaccharide which, after purification, removal of the allyl group, and hydrogenolysis of the benzyl substituents, gave 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-i-deoxy-beta-D-glucopyranosyl)-2-deoxy-alpha-D-glucopyranose. This compound was further converted into di-N-acetyl-hexa-O-acetylchitobiose by acetylation, or into 2-methyl-[4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-3,6-di-O-acetyl-1,2-di-deoxy-alpha-D-glucopyrano]-[2,1-d]-2-oxazoline, a starting material for the preparation of di-N-acetyl-alpha-chitobiosyl phsophate.

UI	MeSH Term	Description	Entries
D008722	Methods	A series of steps taken in order to conduct research.	Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D009682	Magnetic Resonance Spectroscopy	Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING).	In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
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
D009904	Optical Rotation	The rotation of linearly polarized light as it passes through various media.	Optical Activity,Activity, Optical,Rotation, Optical
D010080	Oxazoles	Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.	Oxazole,1,3-Oxazolium-5-Oxides,Munchnones,1,3 Oxazolium 5 Oxides
D004187	Disaccharides	Oligosaccharides containing two monosaccharide units linked by a glycosidic bond.	Disaccharide
D005960	Glucosides	A GLYCOSIDE that is derived from GLUCOSE.	Glucoside
D006027	Glycosides	Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed)	Glycoside
D013055	Spectrophotometry, Infrared	Spectrophotometry in the infrared region, usually for the purpose of chemical analysis through measurement of absorption spectra associated with rotational and vibrational energy levels of molecules. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	IR Spectra,Infrared Spectrophotometry,IR Spectras,Spectra, IR