18423-66-0

Basic information

• Product Name: D-XYLONO-1,4-LACTONE
• Synonyms: D-XYLONO-1,4-LACTONE;D-Xylonic acid-1,4-lactone
• CAS NO: 18423-66-0
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.11
• Mol File: 18423-66-0.mol

Chemical Properties

• Boiling Point: 364.3±11.0 °C(Predicted)
• Appearance: white powder
• Density: 1.667±0.06 g/cm3(Predicted)
• PKA: 12.10±0.60(Predicted)
• CAS DataBase Reference: D-XYLONO-1,4-LACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: D-XYLONO-1,4-LACTONE(18423-66-0)
• EPA Substance Registry System: D-XYLONO-1,4-LACTONE(18423-66-0)

Safety Data

• Hazardous Substances Data: 18423-66-0(Hazardous Substances Data)

Upstream product

• 488-81-3 Adonitol 
• 5346-83-8 calcium D-ribonate 

Downstream Products

• 134877-40-0 3,4-O-benzylidene-D-ribonic-δ-lactone 
• 394739-29-8 (+/-)-Tri-O-acetylarabono-1,4-lactone 

Relevant articles and documents

Stereocontrol in organic synthesis using silicon-containing compounds. Syntheses of (±)-2-deoxyribonolactone and (±)-arabonolactone

Samarium iodide reacts with methyl (Z)-3-dimethyl(4-methylphenyl)silylprop-2-enoate 5b to give dimethyl (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]hexane-1,6-dioate 8b with high stereoselectivity. This meso diester can be converted into (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]pentan-5-olide 16 by Dieckmann cyclisation, demethoxycarbonylation and Baeyer-Villiger reaction. Silyl-to-hydroxy conversion and relactonisation gave (±)-deoxyribonolactone, and anti-selective enolate hydroxylation followed by silyl-to-hydroxy conversion gave (±)-arabonolactone. An attempt to synthesise sugars with the relative configuration (3RS,4RS) was thwarted by an unprecedented retention of configuration at the migration origin in the cationic rearrangement of (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]-5-hydroxypentanoic acid 28 to (3RS,4SR)-3,5-bis[dimethyl(4-methylphenyl)silyl]pentan-1,4-olide 30.

A new efficient access to glycono-1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system

Treatment of unprotected pentitols and hexitols with RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones in 60-96% yield.

Stereoselective Samarium(II)-induced Coupling of β-Silylacrylic Esters: a Synthesis of (+/-)-2-Deoxyribonolactone

Samarium iodide converts the β-silylacrylate 1c with high stereoselectivity into the racemic diester 2c, from which (+/-)deoxyribonolactone 11 can be prepared.

Synthesis of D-erythroascorbic acid from D-glucose

Reaction of a 4:1 mixture of D-ribono- and D-arabinono-1,4-lactones with benzaldehyde and hydrochloric acid gave 59percent crystalline 3,4-O-benzylidene-D-ribono-1,5-lactone.This acetal was oxidized with manganese dioxide in acetone to its 2-keto-derivative (6) in 76percent yield.Acid-catalyzed methanolysis of 6 gave a syrupy mixture of products, which upon tautomerization in hot methanolic sodium acetate followed by removal of sodium ions gave 78percent D-erythroascorbic acid (7).The overall yield of 7 starting from D-glucose was 20percent.