131614-83-0

Basic information

• Product Name: 3,5-O-[(S)-phenylMethylene]-, γ-lactone D-Xylonic acid
• Synonyms: 3,5-O-[(S)-phenylMethylene]-, γ-lactone D-Xylonic acid;3,5-O-[(S)-Phenylmethylene]-D-xylonic acid gamma-lactone
• CAS NO: 131614-83-0
• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.22068
• Mol File: 131614-83-0.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-O-[(S)-phenylMethylene]-, γ-lactone D-Xylonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-O-[(S)-phenylMethylene]-, γ-lactone D-Xylonic acid(131614-83-0)
• EPA Substance Registry System: 3,5-O-[(S)-phenylMethylene]-, γ-lactone D-Xylonic acid(131614-83-0)

Safety Data

• Hazardous Substances Data: 131614-83-0(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 5336-08-3 D-Ribono-1,4-lactone 
• 130481-71-9 Trifluoro-methanesulfonic acid (2S,4aR,7S,7aS)-6-oxo-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl ester 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 15384-37-9 D-xylono-1,4-lactone 
• 87-72-9 D-Xylose 
• 131614-82-9 3,5-O-(S)-benzylidene-D-lyxono-1,4-lactone 
• 15384-34-6 D-lyxono-1,4-lactone 
• 58-86-6 D-xylose 

Downstream Products

• 130481-72-0 (S)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-D-xylono-1,4-lactone 
• 89448-49-7 3,5-O-Benzylidene-2-O-<(methylthio)thiocarbonyl>-D-ribonic Acid γ-Lactone 
• 787572-25-2 methyl 2,4-anhydro-5-deoxy-4-O-benzoyl-D-lyxonate 
• 787572-21-8 methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-D-arabinonate 
• 787572-23-0 methyl 2,4-anhydro-3-azido-5-O-tertbutyldiphenylsilyl-3-deoxy-D-lyxonate 
• 787572-22-9 methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-3-O-trifluoromethanesulfonyl-D-arabinonate 
• 131550-06-6 methyl 2,4-anhydro-(S)-3,5-benzylidene-D-lyxonate 
• 134651-26-6 methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-D-lyxonate 
• 134651-23-3 methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-3-O-trifluoromethanesulfonyl-D-lyxonate 
• 357400-96-5 methyl 2,4-anhydro-5-O-benzyl-D-arabinonate 
• 357400-94-3 methyl 2,4-anhydro-5-O-benzyl-D-lyxonate 
• 357400-98-7 methyl 2,4-anhydro-3-azido-5-O-benzyl-3-deoxy-D-arabinonate 
• 787572-17-2 methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate 
• 357400-97-6 methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-lyxonate 

Relevant articles and documents

Antibacterial activity of xylose-derived LpxC inhibitors – Synthesis, biological evaluation and molecular docking studies

LpxC inhibitors represent a promising class of novel antibiotics selectively combating Gram-negative bacteria. In chiral pool syntheses starting from D- and L-xylose, a series of four 2r,3c,4t-configured C-furanosidic LpxC inhibitors was obtained. The synthesized hydroxamic acids were tested for antibacterial and LpxC inhibitory activity, the acquired biological data were compared with those of previously synthesized C-furanosides, and molecular docking studies were performed to rationalize the observed structure-activity relationships. Additionally, bacterial uptake and susceptibility to efflux pump systems were investigated for the most promising stereoisomers.

Oxetane cis- and trans β-amino-acid scaffolds from d-xylose by efficient SN2 reactions in oxetane rings: Methyl and hydroxymethyl analogues of the antibiotic oxetin, an oxetane β-amino-acid

Highly regioselective reactions of a benzylidene-protected oxetane with (i) triethylsilane-trifluoroacetic acid and (ii) Hanessian-Hullar bromination provide efficient access to 3-hydroxyoxetane carboxylates in which only the C-3 OH is unprotected. Subseq

Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones

The different reactivities of D-ribonolactone, L-arabinonolactone, D-xylonolactone, D-lyxonolactone and 2-deoxy-D-ribonolactone toward benzaldehyde and acetone in acidic media, were examined. The reactions involved complex equilibria and were investigated with extensive 13C NMR studies as well as X-ray crystallographic analysis of selected products. Molecular mechanics (MM2) and semiempirical (PM3 and AM1) calculations of some derivatives were carried out in order to facilitate structural and conformational assignments. The differences in reactivity observed for the reactions of D-pentono-1,4-lactones with benzaldehyde and acetone are rationalized in terms of their structural and conformational features.