15384-34-6

Usage

Uses

Used in Pharmaceutical Synthesis:
D-LYXONO-1,4-LACTONE is used as a key intermediate in the synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol, which is a glucosidase inhibitor with demonstrated in vitro antiviral activity. This makes it a valuable compound for the development of new antiviral medications.
Used in Organic Synthesis:
D-LYXONO-1,4-LACTONE is also utilized as a compound in organic synthesis, where it can be employed to create a range of other chemical products. Its versatility in this field makes it an important component in the development of new materials and substances for various applications across different industries.

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

• 526-92-1 D-lyxonic acid 
• 78138-87-1 potassium D-lyxonate 
• 532-20-7 D-lyxose 
• 67-56-1 methanol 
• 77-76-9 2,2-dimethoxy-propane 
• 488-81-3 Adonitol 
• 5346-83-8 calcium D-ribonate 
• 32449-92-6 D-glucurono-6,3-lactone 
• 1114-34-7 D-lyxose 
• 10257-28-0 D-Galactose 
• 728879-26-3 D-arabinuronic acid 
• 910881-68-4 D-lyxonic acid hydrazide 

Downstream Products

• 1114-34-7 D-lyxose 
• 79580-61-3 tri-O-acetyl-D-lyxono-1,4-lactone 
• 131614-82-9 3,5-O-(S)-benzylidene-D-lyxono-1,4-lactone 
• 56543-11-4 3,5-O-isopropylidene-D-lyxono-1,4-lactone 
• 56543-10-3 2,3-O-isopropylidene-D-lyxono-1,4-lactone 
• 149466-59-1 3,5(S)-O-benzylidene-2-O-methanesulphonyl-D-lyxono-1,4-lactone 
• 394739-29-8 (+/-)-Tri-O-acetylarabono-1,4-lactone 
• 134877-40-0 3,4-O-benzylidene-D-ribonic-δ-lactone 
• 179992-61-1 (2S,4aR,7R,7aR)-7-Azido-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one 
• 1281872-13-6 2-azido-3,5-O-benzylidene-2-deoxy-D-lyxitol 
• 38996-14-4 (4R,5S)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 50270-80-9 tri-O-benzoyl-2-bromo-2-deoxy-D-xylopyranose 
• 56247-00-8 di-O-benzoyl-2-bromo-2-deoxy-D-xylopyranosyl bromide 
• 26532-13-8 methyl 2,5-di-O-benzoyl-3-deoxy-α-D-threo-pentofuranoside 

Relevant academic research and scientific papers

Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives

Treatment of unprotected D-ribono, D-arabinono and D-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%-95% yields. Under the same conditions, D-lyxono-1,4-lactone resulted in the 2-halogeno compounds.

New approach to (-)-polyoxamic acid and 3,4-diepipolyoxamic acid from d-lyxono-1,4-lactone

The non-natural enantiomer of polyoxamic acid (1) and 3,4-diepipolyoxamic acid (2) was synthesized in four steps from d-lyxono-1,4-lactone (4). Regioselective bromination of unprotected d-lyxono-1,4-lactone with HBr/AcOH led to 2-bromo-2-deoxy-d-xylono-1,

Prebiotic synthesis of 2-deoxy-d-ribose from interstellar building blocks promoted by amino esters or amino nitriles

Understanding the prebiotic genesis of 2-deoxy-d-ribose, which forms the backbone of DNA, is of crucial importance to unravelling the origins of life, yet remains open to debate. Here we demonstrate that 20 mol% of proteinogenic amino esters promote the selective formation of 2-deoxy-d-ribose over 2-deoxy-d-threopentose in combined yields of ≥4%. We also demonstrate the first aldol reaction promoted by prebiotically-relevant proteinogenic amino nitriles (20 mol%) for the enantioselective synthesis of d-glyceraldehyde with 6% ee, and its subsequent conversion into 2-deoxy-d-ribose in yields of ≥ 5%. Finally, we explore the combination of these two steps in a one-pot process using 20 mol% of an amino ester or amino nitrile promoter. It is hence demonstrated that three interstellar starting materials, when mixed together with an appropriate promoter, can directly lead to the formation of a mixture of higher carbohydrates, including 2-deoxy-d-ribose.

GLYCOSIDASE INHIBITORS AND USES THEREOF

The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related t

A heterogeneous Pd-Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars

A critical step in the synthesis of the rare sugars, l-lyxose and l-ribose, from the corresponding d-sugars is the oxidation to the lactone. Instead of conventional oxidizing agents like bromine or pyridinium dichromate, it was found that a heterogeneous catalyst, Pd-Bi/C, could be used for the direct oxidation with molecular oxygen. The composition of the catalyst was optimized and the best results were obtained with 5:1 atomic ratio of Pd:Bi. The overall yields of the five-step procedure to l-ribose and l-lyxose were 47% and 50%, respectively. The synthetic procedure is advantageous from the viewpoint of overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the heterogeneous oxidation catalyst can be easily separated from the reaction mixture and reused with no loss of activity.

Process and intermediate compounds for the preparation of pyrrolidines

Processes for the preparation of pyrrolidones (7 and 8) and pyrrolidines (9 and 10) from tri-O-acetyl-D-erythro-4-pentulosonic acid esters are described. The compounds are aza sugar analogs of D-ribofuranoside and are intermediates to drugs which regulate nucleoside and nucleic acid synthesis.

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.

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.

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.