D-galactonolactone

Base Information

• Chemical Name: D-galactonolactone
• CAS No.: 15892-28-1
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.142
• DSSTox Substance ID: DTXSID401313563
• Nikkaji Number: J426.673K
• Wikidata: Q27098313
• Metabolomics Workbench ID: 50321

Synonyms:D-galactonolactone;D-Galactono-1,5-lactone;15892-28-1;D-galactonic acid delta-lactone;D-Galactono-8-lactone;(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one;(3R,4S,5R,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one;D-GALCTOPYRANOSYL-1-ON;3vdb;3i3b;3mv0;3t0d;3t2q;delta-D-Galactonolactone;SCHEMBL2461264;CHEBI:15945;3t09;DTXSID401313563;DB01885;C02669;Q27098313;WURCS=2.0/1,1,0/[A2112h_1-5]/1/

Chemical Property of D-galactonolactone

Chemical Property:

• Vapor Pressure: 7.6E-10mmHg at 25°C
• XLogP3: -2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 178.04773803
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(C1C(C(C(C(=O)O1)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@@H]([C@@H]([C@H](C(=O)O1)O)O)O)O

Technology Process of D-galactonolactone

There total 9 articles about D-galactonolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

L-allonic acid (740753-96-2) → L-allonic acid-5-lactone (90-80-2,7506-65-2,10366-75-3,15892-28-1,32746-79-5,52153-09-0,52393-78-9,110115-45-2,120523-34-4,124819-01-8,124915-65-7,1335-57-5,4253-68-3)

Guidance literature:

With ethanol; schnelles Eindampfen unter vermindertem Druck und Behandeln des Rueckstands mit wasserfreiem Aethanol;

Reference yield:

D-Galactose (10257-28-0) → D-galactono-1,4-lactone (2782-07-2) + (3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one (15892-28-1,1335-57-5,4253-68-3)

Guidance literature:

[(C₄Ph₄CO)(CO)2Ru]2; In cyclohexanone; N,N-dimethyl-formamide; at 21 ℃; for 87h; Title compound not separated from byproducts;

DOI:10.1002/ejoc.200300761

Reference yield:

D-galactonic acid (133-42-6,488-33-5,526-95-4,526-97-6,576-36-3,642-99-9,1114-17-6,3956-93-2,6906-37-2,7760-07-8,13382-27-9,20246-33-7,20246-35-9,20246-52-0,20246-53-1,21675-42-3,22430-69-9,24871-35-0,28223-42-9,28278-17-3,51547-37-6) → D-galactono-1,4-lactone (2782-07-2) + (3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one (15892-28-1,1335-57-5,4253-68-3)

Guidance literature:

With hydrogenchloride; water; at 25 ℃;

upstream raw materials:

L-allonic acid

D-galactonic acid

D-Galactose

D-Galactose

Downstream raw materials:

3-(D-galacto-pentitol-1-yl)-4-(p-nitrobenzylidene)amino-5-mercapto-4H-1,2,4-triazole

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

Refernces

Microwave-assisted organic synthesis of 3-(D-Gluco-pentitol-1-YL)-1H-1,2,4- triazole

10.1080/15257770500544545

The research focuses on the microwave-assisted organic synthesis (MAOS) of 3-(D-gluco-pentitol-1-yl)-1H-1,2,4-triazole, a compound of interest in medicinal chemistry due to its pharmacological activities. The study aims to accelerate the synthesis of seco C-nucleosides of 1,2,4-triazole using microwave irradiation, which is reported to provide higher yields and purities compared to traditional synthetic methods. The chemicals used in the process include D-glucono- and D-galactono-1,5-lactones, thiocarbohydrazide, p-nitrobenzaldehyde, ethyl chloroacetate, and various reagents for subsequent reactions such as acetic anhydride, sodium acetate, and ammonium hydroxide. The conclusions of the research indicate that microwave irradiation significantly accelerates the synthesis of the target compounds, improving yields and reducing reaction times, thus demonstrating the effectiveness of MAOS in the synthesis of these potentially medicinally important compounds.

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