131139-12-3

Basic information

• Product Name: methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate
• Synonyms: methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate
• CAS NO: 131139-12-3
• Molecular Weight: 342.392
• Mol File: 131139-12-3.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate(131139-12-3)
• EPA Substance Registry System: methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate(131139-12-3)

Safety Data

• Hazardous Substances Data: 131139-12-3(Hazardous Substances Data)

Upstream product

• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 120693-82-5 3,5-Di-O-benzyl-α-D-xylofuranose 
• 41341-99-5 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 100-39-0 benzyl bromide 
• 16054-77-6 3,5-di-O-benzyl-D-xylofuranose 
• 131139-04-3 (3R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxydihydrofuran-2(3H)-one 
• 67-56-1 methanol 
• 131139-08-7 3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone 

Downstream Products

• 146820-75-9 2,4-anhydro-3,5-di-O-benzyl-D-lyxonic acid 
• 131139-17-8 (2R,4R)-3-Benzyloxy-2,4-bis-benzyloxymethyl-oxetane 
• 161856-73-1 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(2R,3R,4R)-2-methoxycarbonyl-4-(toluene-4-sulfonyloxymethyl)-oxetan-3-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 195000-99-8 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2R,3S,4R)-2-hydroxymethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 195001-00-4 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 195000-95-4 (4R,5S,6S)-3-((2R,3R,4R)-2-Azidomethyl-4-methoxycarbonyl-oxetan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 195000-97-6 (4R,5S,6S)-3-((2R,3R,4R)-2-Dimethylcarbamoyl-4-hydroxymethyl-oxetan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 195000-93-2 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-((2R,3R,4R)-2-hydroxymethyl-4-methoxycarbonyl-oxetan-3-ylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 195000-88-5 (2R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzylsulfanyl)-oxetane-2-carboxylic acid dimethylamide 
• 195000-61-4 (2R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzylsulfanyl)-oxetane-2-carboxylic acid methyl ester 
• 195000-65-8 (2R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzylsulfanyl)-oxetane-2-carbaldehyde 
• 161856-71-9 (2R,3R,4R)-3-Acetylsulfanyl-4-(toluene-4-sulfonyloxymethyl)-oxetane-2-carboxylic acid methyl ester 
• 161856-72-0 2,4-Anhydro-3-thio-D-arabinonic Acid Methyl Ester 5-(4-Methylbenzenesulfonate) 
• 161856-70-8 2,4-Anhydro-D-lyxonic acid Methyl Ester 5-(4-Methylbenzenesulfonate) 

Relevant articles and documents

Oxetane δ-amino acids: Chemoenzymatic synthesis of 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonic acid

Starting from 1,2-O-isopropylidene-D-xylose, methyl 2,4-anhydro-3,5-di-O- benzyl-D-lyxonate (4) was synthesized. Debenzylation and transformation of the primary hydroxyl group yielded methyl 2,4-anhydro-5- N-(t-butoxycarbonyl)amino- D-lyxonate (9). While

Ring contraction of 2-O-trifluoromethanesulphonates of α-hydroxy-γ-lactones to oxetane carboxylic esters

2-O-Trifluoromethanesulphonate esters of the four diastereomeric 3,5-di-O-benzyl-pentono-1,4-lactones gave, on treatment with potassium carbonate in methanol, efficient ring contraction to methyl oxetane-2-carboxylic esters. The stereochemistry at C-2 of