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
• Article Data: 8

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

Description

L-Lyxono-1,4-lactone is an organic compound that serves as a key intermediate in the synthesis of various biologically active molecules. It is characterized by its unique chemical structure, which allows it to participate in a range of reactions and contribute to the formation of complex organic compounds.

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

• 134877-40-0 3,4-O-benzylidene-D-ribonic-δ-lactone 
• 394739-29-8 (+/-)-Tri-O-acetylarabono-1,4-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 
• 443127-30-8 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxono-γ-lactone 
• 443127-32-0 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxitol 
• 443127-34-2 2,3-bis-O-tert-butyldimethylsilyl-1,4-bis-O-methanesulfonyl-5-O-triphenylmethyl-L-lyxitol 
• 1281872-15-8 2-azido-3,5-O-benzylidene-2-deoxy-L-lyxitol 
• 1394842-57-9 C₁₈H₂₆O₅Si 

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.

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.

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.