Biomaterial Database

Stereoselective total synthesis of methyl alpha-D and alpha-L-glucopyranosides. 1977

O Achmatowicz, and R Bielski

Methyl alpha-L- and alpha-D-glucopyranosides have been synthesized from methyl (R)- and (S)-(2-furyl)glycolates (3), respectively. The key intermediates, methyl 6-O-benzyl-2,3-dideoxy-L(and D)-hex-2-enopyranosid-4-uloses (13), were obtained in seven steps from the ester 3, without change of configuration of the asymmetric center, which became C-5 in the sugar molecule. Reduction of the ketone group at C-4 in the glycoside 13 with sodium borohydride afforded the corresponding methyl 6-O-benzyl-2,3-dideoxy-erythro-hex-2-enopyranosides (14). Epoxidation of the double bond in 14, followed by oxirane ring-opening in the anhydro sugar 16, and subsequent catalytic hydrogenolysis of the benzyl group led to the title compounds.

UI	MeSH Term	Description	Entries
D008757	Methylglucosides		Methylglucopyranosides
D008759	Methylglycosides
D002621	Chemistry	A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D005663	Furans	Compounds with a 5-membered ring of four carbons and an oxygen. They are aromatic heterocycles. The reduced form is tetrahydrofuran.	Tetrahydrofurans
D006016	Glycolates	Derivatives of ACETIC ACID which contain an hydroxy group attached to the methyl carbon.	2-Hydroxyacetates,Glycolate Ethers,Hydroxyacetate Ethers,Hydroxyacetates,Hydroxyacetic Acids,2 Hydroxyacetates,Acids, Hydroxyacetic,Ethers, Glycolate,Ethers, Hydroxyacetate
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D055598	Chemical Phenomena	The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes.	Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical