104196-15-8

Basic information

• Product Name: L-Lyxono-1,4-lactone
• Synonyms: L-Lyxono-1,4-lactone;L-Lyxonic Acid γ-Lactone
• CAS NO: 104196-15-8
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.11402
• Product Categories: Carbohydrates & Derivatives
• Mol File: 104196-15-8.mol

Chemical Properties

• Boiling Point: 364.3±11.0 °C(Predicted)
• Appearance: /
• Density: 1.667±0.06 g/cm3 (20 ºC 760 Torr)
• PKA: 12.10±0.60(Predicted)
• CAS DataBase Reference: L-Lyxono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: L-Lyxono-1,4-lactone(104196-15-8)
• EPA Substance Registry System: L-Lyxono-1,4-lactone(104196-15-8)

Safety Data

• Hazardous Substances Data: 104196-15-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
L-Lyxono-1,4-lactone is used as a synthetic building block for the creation of 2-Acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol (LABNAc), a potent pyrrolidine inhibitor of hexosaminidases. This application is significant in the development of treatments for various diseases, as hexosaminidase inhibitors can help regulate enzyme activity and potentially mitigate the effects of certain conditions.
Used in Organic Synthesis:
L-Lyxono-1,4-lactone is also a compound useful in organic synthesis, where it can be employed to produce a variety of complex organic molecules. Its versatility in participating in different types of chemical reactions makes it a valuable component in the synthesis of a wide range of compounds, from pharmaceuticals to specialty chemicals.

Upstream product

• 488-81-3 Adonitol 
• 5346-83-8 calcium D-ribonate 
• 1949-78-6 L-lyxose 
• 7643-75-6 L-(-)-arabitol 
• 58-86-6 D-xylose 
• 945622-68-4 4-O-methanesulfonyl-2,3,5-tri-O-pivaloyl-D-ribonitrile 

Downstream Products

• 394739-29-8 (+/-)-Tri-O-acetylarabono-1,4-lactone 
• 134877-40-0 3,4-O-benzylidene-D-ribonic-δ-lactone 
• 443127-29-5 5-O-triphenylmethyl-L-lyxono-γ-lactone 
• 1021178-24-4 benzylidene-L-lyxono-1,4-lactone 
• 944329-25-3 C₁₂H₁₁N₃O₄ 
• 944329-27-5 C₁₂H₁₆N₄O₂ 
• 944329-28-6 N-((3R,4S,5R)-1-benzyl-4-hydroxy-5-(hydroxymethyl)pyrrolidin-3-yl)acetamide 
• 944329-24-2 2-acetamido-1,4-imino-1,2,4-trideoxy-D-arabinitol 
• 1281872-15-8 2-azido-3,5-O-benzylidene-2-deoxy-L-lyxitol 
• 1394842-57-9 C₁₈H₂₆O₅Si 
• 443127-34-2 2,3-bis-O-tert-butyldimethylsilyl-1,4-bis-O-methanesulfonyl-5-O-triphenylmethyl-L-lyxitol 
• 443127-32-0 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxitol 
• 443127-30-8 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxono-γ-lactone 

Relevant articles and documents

A facile and general synthesis of rare L-sugar lactones

A facile and general synthesis of rare L-sugar lactones from D-sugars by selectively inverting C-5 was developed. Selective 1-deacylation of sugar perpivaloates by hydroxylamine is described. More practically, β-D-glucose pentaacetate could be transformed to L-idono-1,4-lactones by this simple procedure. Georg Thieme Verlag Stuttgart.

Supramolecular assemblies of diacetylenic aldonamides

The study of novel amphiphiles that form nonspheroidal assemblies upon hydration is fundamental to understanding the relationship between molecular structure and supramolecular morphology. Structural components of previously reported amphiphiles were used to design the single chain diacetylenic aldonamides reported here. Open chain sugar headgroups were linked via an amide bond to a hydrophobic tail. Diacetylenes were incorporated in the alkyl chain both as a structural component and as a reactive unit. Photopolymerization was used to test the molecular ordering of the hydrophobic region of the assemblies and to enhance their thermal and chemical stability. The electron density of the diacetylenes allowed direct imaging of the assemblies by TEM. The morphology and reactivity of a series of N-dodeca-5,7-diynylaldonamides were determined. The aldonamides were derived from two aldoheptoses, o-glycero-D-gluconamide and D-glycero-L-mannonamide; four aldohexoses, D-galactonamide, D-gluconamide, L-mannonamide, and D-gulonomide; two aldopentoses, L-arbanonamide and L-lyxonamide; and two aldotetroses, L-threonamide and D-erythronamide. W-Dodecylaldonamide analogues were prepared and examined to evaluate the importance of the diacetylene group on the morphology. The microscopy and molecular modeling data indicate that at least two packing arrangements for these assemblies are possible. One is the head-to-head bilayer packing typical of most amphiphilic molecules; the other is a head-to-tail arrangement. The head-to-head packing results in assemblies which are planar, helical, or tubular. The head-to-tail packing arrangement and "dromic" hydrogen-bonding patterns are associated with fiber-like supramolecular assemblies. Numerous potential applications of tubule microstructures have been proposed. The relative ease of preparation of many of these aldonamide molecules and their assemblies recommends them for many of these applications.

Toward a general strategy for the synthesis of 3,4-dihydroxyprolines from pentose sugars

A general strategy is proposed, wherein a pentose sugar γ-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-D-2,3-cis-3, 4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-cis-3, 4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl- 3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.

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.

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.