Nojirimycin

Base Information

• Chemical Name: Nojirimycin
• CAS No.: 15218-38-9
• Molecular Formula: C6H13 N O5
• Molecular Weight: 179.173
• Hs Code.: 2922399090
• Nikkaji Number: J15.857G
• Wikipedia: Nojirimycin
• Wikidata: Q27103975
• Metabolomics Workbench ID: 51895
• ChEMBL ID: CHEMBL120638
• Mol file: 15218-38-9.mol

Synonyms:5-amino-D-glucose;nojirimycin;nojirimycin sulfate (2:1);nojirimycin sulfite (1:1);nojirimycin, (alpha)-isomer

Chemical Property of Nojirimycin

Chemical Property:

• Vapor Pressure: 7.48E-08mmHg at 25°C
• Boiling Point: 394.3°Cat760mmHg
• Flash Point: 214.3°C
• PSA: 113.18000
• Density: 1.643g/cm³
• LogP: -3.31960
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 179.07937252
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

6-AMINO-6-DEOXY-D-GLUCOPYRANOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(N1)O)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H](C(N1)O)O)O)O)O

Technology Process of Nojirimycin

There total 36 articles about Nojirimycin 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: 92.0%

(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((4R,5S)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (138319-95-6) → (-)-galactostatin (15218-38-9,19130-94-0,62362-40-7,107537-94-0,108147-56-4,109718-63-0,109718-64-1,109718-65-2,121251-50-1,126575-57-3,138382-48-6,149406-05-3)

Guidance literature:

With trifluoroacetic acid; for 0.5h; Ambient temperature;

DOI:10.1039/c39910001576

Reference yield: 92.0%

5-amino-5-deoxy-D-glucose hydrogen sulfite (19130-95-1) → nojirimycin (15218-38-9)

Guidance literature:

With Dowex (OH^(1-)); In water; for 0.75h;

DOI:10.1002/hlca.19820650403

Reference yield: 90.0%

5-amino-5-deoxy-D-glucose-1-sulfonic acid (81703-56-2) → (+)-nojirimycin (15218-38-9)

Guidance literature:

With water;

DOI:10.1021/jo00391a031

upstream raw materials:

5-amino-5-deoxy-D-glucose hydrogen sulfite

5-amino-5-deoxy-D-glucose-1-sulfonic acid

(3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

1-Desoxynojirimycin-1-sulfonsaeure

Downstream raw materials:

1,5-dideoxy-1,5-imino-D-glucitol

nojirimycin-δ-lactam

Refernces

Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide

10.1016/j.tetasy.2010.01.007

Vrushali H. Jadhav et al. describe a method for synthesizing azepane and nojirimycin iminosugars using the Sharpless asymmetric epoxidation of D-glucose-derived allyl alcohol. The researchers achieved high stereoselectivity in the formation of a- and ?-epoxides, which were then selectively opened with sodium azide to predominantly form 6-azido diols over 5-azido diols. These azido diols were subsequently converted into the corresponding seven-membered azepane and six-membered nojirimycin iminosugars. The study highlights the importance of these iminosugars as glycosidase inhibitors with potential applications in treating diseases like diabetes, cancer, and viral infections. The authors also discuss the challenges and ongoing efforts to improve the regioselectivity of the epoxide ring opening to favor the formation of 5-azido diols, which could further enhance the synthesis of these bioactive compounds.

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