15384-37-9

Usage

Uses

Used in Pharmaceutical Industry:
D-XYLONO-1,4-LACTONE is used as a key intermediate for the synthesis of zaragozic acids, which are important in the inhibition of sterol synthesis in Saccharomyces cerevisiae. This application is significant for the development of drugs targeting fungal infections and other conditions related to sterol synthesis dysregulation.
Used in Chemical Synthesis:
D-XYLONO-1,4-LACTONE is used as a versatile building block in the synthesis of various bioactive compounds and pharmaceuticals. Its ability to undergo [1,2]-Wittig rearrangement makes it a valuable asset in the creation of complex molecular structures with potential applications in medicine and other fields.

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

• 87-72-9 D-Xylose 
• 532-20-7 D-xylofuranose 
• 58-86-6 D-xylose 
• 488-81-3 Adonitol 
• 5346-83-8 calcium D-ribonate 
• 488-30-2 D-xylonic acid 

Downstream Products

• 79580-60-2 (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone 
• 87-99-0 XYLITOL 
• 107-93-7 (E)-but-2-enoic acid 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 131614-83-0 (2S,4aR,7R,7aR)-7-hydroxy-2-phenyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one 
• 488-30-2 D-xylonic acid 
• 82796-87-0 D-xylono-1,5-lactone 
• 58-86-6 D-xylose 
• 799277-48-8 5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-xylono-1,4-lactone 
• 26532-13-8 methyl 2,5-di-O-benzoyl-3-deoxy-α-D-threo-pentofuranoside 
• 20603-35-4 2,4;3,5-di-O-benzylidene-D-xylonic Acid 
• 131550-06-6 methyl 2,4-anhydro-3,5-O-benzylidene-D-lyxonate 
• 1310357-30-2 (((4R,5R)-4-((S,Z)-5-(benzyloxy)-1-methoxy-3-methylpent-2-en-1-yl)-2,2-dimethyl-1,3-dioxan-5-yl)oxy)triethylsilane 
• 1310357-42-6 (((4R,5R)-4-((S,E)-5-(benzyloxy)-1-methoxy-3-methylpent-2-en-1-yl)-2,2-dimethyl-1,3-dioxan-5-yl)oxy)triethylsilane 

Relevant academic research and scientific papers

Acidity and lactonization of xylonic acid: A nuclear magnetic resonance study

In acidic aqueous solutions the xylonic acid/xylonate equilibrium is coupled with the formation of the γ-and δ-lactones. The γ-lactone is formed more readily, whereas the Δ5-lactone can only be observed in traces at very low pH values (13C NMR, both the lactone hydrolization constant and the acid dissociation constant could be determined (KL = 4.08, pKa1 = 3.65 ± 0.34). Further, a second deprotonation of one of the hydroxyl groups could be observed at very high pH (pKa2 = 13.3 ± 0.76). Copyright Taylor & Francis Group, LLC.

Stereoselective Palladium-Catalyzed Arylation of Exo-Glycals with Aryl Iodides

A novel methodology for the arylation of exo-glycals has been developed. A range of exo-glycals underwent reactions with aryl iodides in the presence of a palladium catalyst. The transformation proceeded in a stereoselective manner to afford Z-isomers. Th

Converging conversion - using promiscuous biocatalysts for the cell-free synthesis of chemicals from heterogeneous biomass

Production of chemicals from lignocellulosic biomass has been proposed as a suitable replacement to petrochemicals. However, one inherent challenge of biomass utilization is the heterogeneity of the substrate resulting in the presence of mixed sugars after hydrolysis. Fermentation of mixed sugars often leads to poor yield and generation of multiple by-products, thus complicating the subsequent downstream processing. System biocatalysis has thus been developed in recent years to address this challenge. In this work, several novel enzymes with broad substrate promiscuity were identified using a sequence-based discovery approach as suitable biocatalysts in a conversion ofd-xylose andl-arabinose, two major constituents of hemicellulose found in plant biomass. These promiscuous enzymes enabled simultaneous biotransformation ofd-xylose andl-arabinose to yield 1,4-butanediol (BDO) with a maximum production rate of 3 g L?1h?1and a yield of >95%. This model system was further adapted toward the production of α-ketoglutarate (2-KG) from the pentoses using O2as a cosubstrate for cofactor recycling reaching a maximum production rate of 4.2 g L?1h?1and a yield of 99%. To verify the potential applicability of our system, we attempted to scale up the BDO and 2-KG production fromd-xylose andl-arabinose. Simple optimization and reaction engineering allowed us to obtain BDO and 2-KG titers of 18 g L?1and 42 g L?1, with theoretical yields of >75% and >99%, respectively. One of the promiscuous enzymes identified together with auxiliary promiscuous enzymes was also suitable for stereoconvergent synthesis from a mixture ofd-glucose andd-galactose, predominant sugars found in food waste streams and microalgae biomass.

Synthesis and absolute configuration assignment of albucidin: A late-stage reductive deiodination by visible light photocatalysis

The synthesis of albucidin and its enantiomer are described. It involves a visible-light photocatalysis deiodination at the late stage. The absolute configuration of natural albucidin is determined as (1R,3S). This work provides a basis for structural mod

Synthesis of key fragments of leiodelide A

The synthesis of all key fragments of the marine macrolide leiodelide A is described. The polyoxygenated northern subunit is derived from d-xylose, while the southern subunit is rapidly assembled via an aldol reaction and Horner-Wadsworth-Emmons olefination. This highly convergent approach will allow for rapid modification and assembly of several isomers of leiodelide A, which may be necessary considering the assignment of leiodelide B has been previously shown to be incorrect.

Solubilization, purification, and properties of membrane-bound D-glucono-δ-lactone hydrolase from Gluconobacter oxydans

Membrane-bound glucono-δ-lactonase (MGL) was purified to homogeneity from the membrane fraction of Gluconobacter oxydans IFO 3244. After solubilization with 1 M CaCl2, MGL was purified in the presence of Ca2+ and detergent. A single

Synthesis of 3-fluoro-oxetane δ-amino acids

Starting from d-xylose, 2,4-anhydro-5-N-(tert-butoxycarbonyl)amino-5-deoxy- 3-fluoro-d-arabinonic acid 11 was synthesized over 10 steps including ring contraction, fluorination, and ester hydrolysis. Bromine oxidation of d-xylose followed by benzylidenati

Synthesis of beta-L-2'-deoxy nucleosides

An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

Development of a novel synthetic process for 2-deoxy-3,5-di-O-p-toluoyl- α-L-ribofuranosyl chloride: A versatile intermediate in the synthesis of 2′-deoxy-L-ribonucleosides

A novel synthetic route to 2-deoxy-3,5-di-O-p-toluoyl-α-L- ribofuranosyl chloride (1) from inexpensive D-xylose (3) is described. 1 is a key intermediate in the synthesis of the antiviral agent 1-(2-deoxy-β-L- ribofuranosyl)thymine (β-L-thymidine) (2) and

Oxetane cis- and trans β-amino-acid scaffolds from d-xylose by efficient SN2 reactions in oxetane rings: Methyl and hydroxymethyl analogues of the antibiotic oxetin, an oxetane β-amino-acid

Highly regioselective reactions of a benzylidene-protected oxetane with (i) triethylsilane-trifluoroacetic acid and (ii) Hanessian-Hullar bromination provide efficient access to 3-hydroxyoxetane carboxylates in which only the C-3 OH is unprotected. Subseq