154096-13-6

Basic information

• Product Name: (2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-2,3-dihydrofuran
• Synonyms: (2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-2,3-dihydrofuran
• CAS NO: 154096-13-6
• Molecular Weight: 296.366
• Mol File: 154096-13-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-2,3-dihydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-2,3-dihydrofuran(154096-13-6)
• EPA Substance Registry System: (2R,3S)-3-(benzyloxy)-2-((benzyloxy)methyl)-2,3-dihydrofuran(154096-13-6)

Safety Data

• Hazardous Substances Data: 154096-13-6(Hazardous Substances Data)

Upstream product

• 50-69-1 D-ribose 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 100-39-0 benzyl bromide 
• 10226-94-5 ((2R,3S)-3-acetoxy-2,3-dihydrofuran-2-yl)methyl acetate 
• 6160-50-5 3,5-di-O-benzyl-2-deoxy-D-ribofuranose 
• 6160-49-2 1-O-acetyl-3,5-di-O-benzyl-2-deoxy-D-erythro-pentofuranose 
• 58166-67-9 2,3-O-Isopropylidene-5-O-trityl-α,β-ribofuranosyl chloride 
• 96761-00-1 1,4-anhydro-2-deoxy-D-erythro-pent-1-enitol 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 50-89-5 thymidine 
• 132487-16-2 methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside 
• 334784-80-4 (2R,3R,4S)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran 
• 334784-79-1 (2R,3R,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran 
• 254445-37-9 Phenyl 3,5-di-O-benzyl-2-deoxy-1-seleno-D-ribofuranoside 

Downstream Products

• 349654-67-7 β-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine 
• 349654-66-6 α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine 
• 349654-65-5 1'-O-Acetyl-2'-deoxy-2'-difluoromethyl-3',5'-di-O-benzyl-α-D-arabinose 
• 544429-10-9 Acetic acid (2R,3R,4R,5R)-4-benzyloxy-5-benzyloxymethyl-2-(diethoxy-phosphorylmethyl)-2-oxo-2λ⁵-[1,2]oxaphospholan-3-yl ester 
• 544429-09-6 [((2R,3R)-2,4-Bis-benzyloxy-1,3-dihydroxy-butyl)-hydroxy-phosphinoylmethyl]-phosphonic acid diethyl ester 
• 544429-08-5 (2R,3R)-3-hydroxy-2,3-bis(benzylyloxy)propionaldehyde 

Relevant articles and documents

Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.

Synthesis of 3′-Deoxy-3′-difluoromethyluridine and 2′-Deoxy-2′difluoromethyluridine

The synthesis of 3′-deoxy-3′-difluoromethyluridine (9) and 2′-deoxy-2′-difluoromethyluridine (7β) by hydrogenation of the corresponding difluoromethylene derivatives is described. A second synthesis of the latter has been performed. Starting from thymidine, a two-step procedure affords the benzylated furanoid glycal 12. Addition of dibromodifluoromethane gives the α-2′-deoxy-2′bromodifluoromethylarabinose (13). This compound allowed an access to α- or β -2′-deoxy-2′-difluoromethyluridine via a SN2 type reaction on a α-halodeoxyarabinose species.

Synthesis of erythro and threo furanoid glycals using 5-endo-trig selenoetherification as key step

Differently protected erythro and threo furanoid glycals were synthesised from 4-pentene-1,2,3-triol, through selenium induced 5-endo-trig cyclization and selenoxide elimination.