51532-86-6

Usage

InChI:InChI=1/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4+/m0/s1

Upstream product

• 7643-75-6 L-(-)-arabitol 
• 488-81-3 Adonitol 
• 5346-83-8 calcium D-ribonate 

Downstream Products

• 16751-39-6 2,3,5-Tri-O-acetyl-L-arabino-1,4-lacton 
• 312700-00-8 L-arabinonic acid anilide 
• 496-64-0 3-hydroxy-2-pyrone 
• 88-14-2 2-furanoic acid 
• 710941-59-6 L-ribonic acid 
• 261967-42-4 (2R,3R,4S)-2,3-dihydroxy-5-trityloxy-4-pentanolide 
• 261967-52-6 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-arabino-γ-lactone 
• 443127-31-9 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-arabinitol 
• 443127-33-1 2,3-bis-O-tert-butyldimethylsilyl-1,4-bis-O-methanesulfonyl-5-O-triphenylmethyl-L-arabinitol 
• 172603-62-2 2-O-benzoyl-L-glycero-pent-2-enono-1,4-lactone 
• 172603-61-1 2-O-benzoyl-5-O-tert-butyldiphenylsilyl-L-glycero-pent-2-enono-1,4-lactone 
• 394739-29-8 (+/-)-Tri-O-acetylarabono-1,4-lactone 
• 134877-40-0 3,4-O-benzylidene-D-ribonic-δ-lactone 

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.