133908-85-7

Basic information

• Product Name: L-Ribono-1,4-lactone
• Synonyms: L-Ribono-1,4-lactone
• CAS NO: 133908-85-7
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.11402
• Mol File: 133908-85-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Ribono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: L-Ribono-1,4-lactone(133908-85-7)
• EPA Substance Registry System: L-Ribono-1,4-lactone(133908-85-7)

Safety Data

• Hazardous Substances Data: 133908-85-7(Hazardous Substances Data)

Usage

Description

L-Ribono-1,4-lactone is a chemical compound that is an analog of D-Ribonolactone. It is known for its ability to inhibit the β-galactosidase enzyme found in E. coli.

Uses

Used in Pharmaceutical Industry:
L-Ribono-1,4-lactone is used as an enzyme inhibitor for β-galactosidase in E. coli, which can be beneficial in the development of treatments targeting bacterial infections or in research applications where controlling the activity of this enzyme is necessary.
Used in Research Applications:
L-Ribono-1,4-lactone is used as a research tool to study the function and regulation of β-galactosidase enzyme in various biological processes. This can help scientists understand the role of this enzyme in different diseases and conditions, potentially leading to the discovery of new therapeutic targets.

Upstream product

• 54622-95-6 (3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid 
• 532-20-7 D-Ribose 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 488-81-3 Adonitol 
• 5346-83-8 calcium D-ribonate 
• 710941-59-6 L-ribonic acid 

Downstream Products

• 394739-29-8 (+/-)-Tri-O-acetylarabono-1,4-lactone 
• 134877-40-0 3,4-O-benzylidene-D-ribonic-δ-lactone 
• 10374-51-3 5-hydroxymethyl-4,5-dihydrofuranone 
• 419568-67-5 (2R,3S,4R,5S,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol 
• 24259-59-4 L-ribose 
• 88-14-2 2-furanoic acid 
• 496-64-0 3-hydroxy-2-pyrone 

Relevant articles and documents

Synthesis of l -Ribose from d -Ribose by a Stereoconversion through Sequential Lactonization as the Key Transformation

l -Ribose, a key precursor of various l -nucleosides can only be synthesized from other sugars or other non-sugar precursors. Herein, the study involves the synthesis of naturally rare l -ribose from readily available d -ribose. Though, many synthetic strategies are developed to meet the increasing demands of l -ribose, seeking innovation, a synthesis employing sequential lactonization as the key transformation was explored. This novel conversion involves protection, oxidation, sequential lactonization, reduction with DIBAL-H, and deprotection..

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.

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.