2782-09-4

Basic information

• Product Name: D-ARABINO-1,4-LACTONE
• Synonyms: D-ARABINO-1,4-LACTONE;D-ARABONIC ACID-GAMMA-LACTONE;D-arabono-1,4-lactone;D-Arabinonic acid γ-lactone;1-Oxo-1-deoxy-D-arabinofuranose;D-Arabinoic acid 1,4-lactone;D-Arabinoic acid γ-lactone;D-arabinono-1,4-lactone
• CAS NO: 2782-09-4
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.11
• Product Categories: Carbohydrates & Derivatives
• Mol File: 2782-09-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 113-114 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 364.3°C at 760 mmHg
• Flash Point: 162.8°C
• Appearance: /
• Density: 1.667g/cm³
• Vapor Pressure: 8.77E-07mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: −20°C
• Solubility: Methanol (Slightly), Water (Sparingly)
• PKA: 12.10±0.60(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: D-ARABINO-1,4-LACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: D-ARABINO-1,4-LACTONE(2782-09-4)
• EPA Substance Registry System: D-ARABINO-1,4-LACTONE(2782-09-4)

Safety Data

• RTECS: CE6100000
• Hazardous Substances Data: 2782-09-4(Hazardous Substances Data)

Usage

Uses

D-Arabinono-1,4-lactone was used as a substrate for the analysis of L-Fucono-1,5-lactonase from cog3618 of amidohydrolase superfamily.

InChI:InChI=1/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4+/m1/s1

Upstream product

• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 67-64-1 acetone 
• 5336-08-3 D-Ribono-1,4-lactone 
• 488-81-3 Adonitol 
• 5346-83-8 calcium D-ribonate 

Downstream Products

• 16751-37-4 2,3,5-tri-O-acetyl-D-arabino-1,4-lactone 
• 15909-68-9 D-arabinonic acid methyl ester 
• 92008-12-3 1-Benzyl-2-D-arabonoyl-hydrazin 
• 394739-29-8 (+/-)-Tri-O-acetylarabono-1,4-lactone 
• 10323-20-3 D-Arabinose 
• 26532-13-8 methyl 2,5-di-O-benzoyl-3-deoxy-α-D-threo-pentofuranoside 
• 917805-74-4 (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid-2-methylpropan-2-amine 
• 808162-99-4 isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 1364244-23-4 5-O-(triphenylmethyl)-3-deoxy-2-O-(methanesulfonyl)-D-threo-pentono-1,4-lactone 
• 1364244-21-2 5-O-(triphenylmethyl)-3-deoxy-2-O-(methanesulfonyl)-D-glyceropent-2-enono-1,4-lactone 
• 1364244-34-7 (3S,5S)-3,5-dihydroxy-6-(trityloxy)hexanenitrile 
• 1364244-32-5 5-O-(triphenylmethyl)-3-deoxy-1,2-anhydro-D-erythro-pentitol 
• 1364244-30-3 5-O-(triphenylmethyl)-3-deoxy-2-O-(methanesulfonyl)-1,4-di-O-acetyl-D-threo-pentitol 
• 1364244-27-8 5-O-(triphenylmethyl)-3-deoxy-2-O-(methanesulfonyl)-D-threo-pentitol 

Relevant articles and documents

SEPARATION OF EPIMERIC γ-ALDONOLACTONES IN THE SYNTHESIS OF RIBOFLAVIN

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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.

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.