5336-08-3

Basic information

• Product Name: D(+)-Ribonic acid gamma-lactone
• Synonyms: D-RIBOSE-LACTONE;D-(+)-RIBONIC ACID GAMMA-LACTON;D(+)-RIBONIC ACID GAMMA-LACTONE;D-(+)-RIBONIC ACID G-LACTONE;D-(+)-RIBONIC GAMMA-LACTONE;D(+)-RIBONO-1,4-LACTONE;D-RIBONO-1,4-LACTONE;D-(+)-RIBONO-GAMMA-LACTONE
• CAS NO: 5336-08-3
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.11
• EINECS: 226-256-5
• Product Categories: Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Ribose;Sugar Acids;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives;Inhibitors
• Mol File: 5336-08-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 85-87 °C(lit.)
• Boiling Point: 188.68°C (rough estimate)
• Flash Point: 162.8°C
• Appearance: White to Pale Yellow/Powder
• Density: 1.2336 (rough estimate)
• Vapor Pressure: 8.77E-07mmHg at 25°C
• Refractive Index: 18 ° (C=1, H2O)
• Storage Temp.: -20°C Freezer
• Solubility: H2O: 0.1 g/mL, clear
• PKA: 12.10±0.60(Predicted)
• Water Solubility: soluble
• Stability: Stable
• BRN: 82057
• CAS DataBase Reference: D(+)-Ribonic acid gamma-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: D(+)-Ribonic acid gamma-lactone(5336-08-3)
• EPA Substance Registry System: D(+)-Ribonic acid gamma-lactone(5336-08-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 5336-08-3(Hazardous Substances Data)

Usage

Description

D(+)-Ribonic acid gamma-lactone, also known as D-ribono-1,4-lactone, is a five-membered form of ribonolactone with D-configuration. It is a white crystalline solid that serves as an important chiral synthon in organic synthesis and is also a compound useful in organic synthesis.

Uses

1. Used in Pharmaceutical Industry:
D(+)-Ribonic acid gamma-lactone is used as an inhibitor of β-galactosidase of E. coli for its potential applications in the development of drugs targeting bacterial infections.
2. Used in Organic Synthesis:
D(+)-Ribonic acid gamma-lactone is used as an important chiral synthon for its role in the synthesis of various organic compounds, contributing to the development of new pharmaceuticals and chemicals.
3. Used in Research and Development:
D(+)-Ribonic acid gamma-lactone is used as a compound useful in organic synthesis, playing a significant role in the research and development of new chemical entities and materials.

Purification Methods

Purify D-(+)-ribonic acid--lactone by recrystallisation from EtOAc. The tribenzoate has m 54-56o (from AcOH), [] D 25 +27o (c 2.37, Me2NCHO), and the 3,5-O-benzylidene derivative has m 230-231.5o (needles from Me2CO-pet ether) and [] D 25 -177o (CHCl3). [Chen & Joulié J Org Chem 49 2168 1984, Zinner & Voigt J Carbohydr Research 7 38 1968.]

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

• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 5346-83-8 calcium D-ribonate 
• 10257-32-6 D-ribose 
• 532-20-7 D-Ribose 
• 78508-91-5 5-benzyloxy-2-hydroxy-3-hydroxy-D-ribonolactone 
• 41162-32-7 2,3,5-tri-O-acetyl-D-ribonic acid γ-lactone 
• 157453-65-1 (3R,4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxy-dihydrofuran-2-one 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 488-81-3 Adonitol 

Downstream Products

• 41162-32-7 2,3,5-tri-O-acetyl-D-ribonic acid γ-lactone 
• 13237-20-2 D-ribonic acid p-toluidide 
• 3051-94-3 3,4-dimethyl-N-ribitylaniline 
• 64339-92-0 D-ribonic acid-(3.4-dimethyl-anilide) 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 50-69-1 D-ribose 
• 110533-61-4 D-erythro-2-deoxy-pentonic acid-(N'-phenyl-hydrazide) 
• 5588-13-6 1-Benzyl-2-D-ribonoyl-hydrazin 
• 92493-90-8 1-(α-Methylphenethyl)-2-D-ribonoylhydrazin 
• 93432-56-5 1-<4-Dimethylamino-benzyl>-2-D-ribonoyl-hydrazin 
• 642-98-8 D-ribonic acid 
• 27304-20-7 2,3-O-cyclohexylidene-γ-D-ribonolactone 
• 102850-44-2 (-)-2,3-O-<(S)-Benzyliden>-D-ribonsaeure-γ-lacton 
• 102850-43-1 (-)-2,3-O-<(R)-Benzyliden>-D-ribonsaeure-γ-lacton 

Relevant articles and documents

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Novel synthesis method for synthesizing remdesivir

The invention discloses a novel synthesis method for synthesizing remdesivir. According to the synthesis method disclosed by the invention, D-ribose is taken as a raw material and is subjected to a series of reactions such as oxidation, cyclohexanone protection, silanization protection, substitution, substitution, deprotection, coupling, deprotection and the like to synthesize the remdesivir. The post-treatment operation is optimized, and the method has the advantages of being short in reaction time, high in yield, low in cost, suitable for industrial production and the like. The structure of the remdesivir provided by the invention is shown in the specification.

High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues

A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.