203632-28-4

Basic information

• Product Name: (2S,3R,4S,5R)-6-Benzyloxy-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
• Synonyms: (2S,3R,4S,5R)-6-Benzyloxy-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS NO: 203632-28-4
• Molecular Weight: 374.39
• Mol File: 203632-28-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R,4S,5R)-6-Benzyloxy-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S,5R)-6-Benzyloxy-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester(203632-28-4)
• EPA Substance Registry System: (2S,3R,4S,5R)-6-Benzyloxy-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester(203632-28-4)

Safety Data

• Hazardous Substances Data: 203632-28-4(Hazardous Substances Data)

Upstream product

• 489-91-8 D-galacturonic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 203632-30-8 (3aR,4S,7R,7aS)-6-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carboxylic acid benzyl ester 
• 203632-29-5 (3aR,4S,7R,7aR)-6-Benzyloxy-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carboxylic acid benzyl ester 

Relevant articles and documents

Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones

Alduronic acid 4,1-, 5,1-, and 5,2-lactones can be specifically obtained when hexuronic and penturonic acids belonging to the erythrose and threose carbohydrate series undergo a tandem β-fragmentation-intramolecular cyclization reaction. In this way, γ-lactones such as 3-O-formyl-1,2-O-isopropylidene-D-threurono-4,1-lactone (38), 3-O-formyl-1,2-di-O-methyl-D-threurono-4,1-lactones (39), or 3-O-formyl-1,2-O-isopropylidene-D-erythrurono-4,1-lactone (41), and δ-lactones such as 1-O-(tert-butyldimethylsilyl)-4-O-formyl-2,3-O-isopropylidene-D-lyxurono-5,1- lactones(40), or 4-O-formyl-1,2,3-tri-O-methyl-D-arabinurono-5,1-lactones(42), or 3-O-benzyl-4-O-formyl-1,2-O-isopropylidene-D-arabinurono-5,1-lactone (43), were obtained. Alternatively, an intermolecular reaction took place when the carboxyl group was lactonized. Thus, 1,4-di-O-acetyl-3-formyl-1-iodo-D-arabinurono-5,2-lactone (45) was prepared from 2,5-di-O-acetyl-D-glucurono-6,3-lactone (37). The reaction is promoted by two different systems: (diacetoxyiodo)benzene (DIB)-iodine, under mild conditions, or diphenylhydroxyselenium acetate (DHSA)-iodine under visible light irradiation. With this new strategy, nor-aldopyranosuronic and aldofuranosuronic acid lactones are formed via 1,5 and 1,6 intramolecular cyclization.