2782-09-4

Usage

Uses

Used in Enzyme Analysis:
D-ARABINO-1,4-LACTONE is used as a substrate for the analysis of L-Fucono-1,5-lactonase, an enzyme from the amidohydrolase superfamily (cog3618). This application is significant for understanding the enzyme's function, specificity, and potential role in various biological processes.

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 
• 10323-20-3 D-Arabinose 
• 799277-39-7 5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-arabino-1,4-lactone 
• 799277-41-1 2,3-bis-O-(methoxymethyl)-5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-arabino-1,4-lactone 
• 26532-13-8 methyl 2,5-di-O-benzoyl-3-deoxy-α-D-threo-pentofuranoside 
• 394739-29-8 (+/-)-Tri-O-acetylarabono-1,4-lactone 
• 134877-40-0 3,4-O-benzylidene-D-ribonic-δ-lactone 
• 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 
• 488-82-4 D-Arabitol 
• 260364-26-9 (4R,5R,7R,8R,9R,10R)-7,8-O-(di-tert-butylsilylene)-8,9,10-trihydroxy-7-hydroxymethyl-4-phenylsulfonyl-9-O-(trimethylsilyl)-1,6-dioxaspiro[4.5]decane 
• 260364-25-8 (4R,5R,7R,8R,9S)-7,8-O-(di-tert-butylsilylene)-8,9-dihydroxy-7-hydroxymethyl-4-phenylsulfonyl-9-O-(trimethylsilyl)-1,6-dioxaspiro[4.5]decan-10-one 

Relevant academic research and scientific papers

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.

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.

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.