Biomaterial Database

The synthesis of 2-acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucose. 1976

M A Shaban, and R W Jeanloz

Condensation of 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide with 2-amino-2-N,3-O-carbonyl-5.6-O-isopropylidene-D-glucose diethyl acetal gave, unexpectedly, 2-amino-2-N,3-O-carbonyl-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl)-5,6-O-isopropylidene-D-glucose diethyl acetal, futher transformed, by de-esterification followed by acetylation, into the previously known 2-amino-2-N,3-O-carbonyl-2-deoxy-5,6-O-isopropylidene-4-O-alpha-D-mannopyranosyl-D-glucose diethyl acetal and its tetra-O-acetyl derivative. Benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside was condensed with 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl bromide to give benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside. Removal of the 2-O-acetyl group, followed by oxidation with acetic anhydridedimethyl sulfoxide, gave a beta-D-arabino-hexosid-2-ulose (25). After reduction with sodium borohydride, removal of the benzyl groups gave crystalline 2-acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucose (27). The anomeric configuration of the glycosidic linkage was ascertained by comparison with the alpha-D-linked disaccharide.

UI	MeSH Term	Description	Entries
D008358	Mannose	A hexose or fermentable monosaccharide and isomer of glucose from manna, the ash Fraxinus ornus and related plants. (From Grant & Hackh's Chemical Dictionary, 5th ed & Random House Unabridged Dictionary, 2d ed)	D-Mannose,Mannopyranose,Mannopyranoside,D Mannose
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
D009904	Optical Rotation	The rotation of linearly polarized light as it passes through various media.	Optical Activity,Activity, Optical,Rotation, Optical
D004187	Disaccharides	Oligosaccharides containing two monosaccharide units linked by a glycosidic bond.	Disaccharide
D005947	Glucose	A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement.	Dextrose,Anhydrous Dextrose,D-Glucose,Glucose Monohydrate,Glucose, (DL)-Isomer,Glucose, (alpha-D)-Isomer,Glucose, (beta-D)-Isomer,D Glucose,Dextrose, Anhydrous,Monohydrate, Glucose
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
D006595	Hexosamines	AMINO SUGARS created by adding an amine group to a hexose sugar.	Hexosamine