2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one

Base Information

• Chemical Name: 2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one
• CAS No.: 152-93-2
• Molecular Formula: C10H16 N4 O7
• Molecular Weight: 304.26
• Mol file: 152-93-2.mol

Synonyms:Vicine(6CI,7CI,8CI); Divicine b-D-glucopyranoside; NSC 95092; Vicioside

Chemical Property of 2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one

Chemical Property:

• Vapor Pressure: 2.26E-18mmHg at 25°C
• Melting Point: 242-244℃
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 627.4°Cat760mmHg
• PKA: 9.56±0.50(Predicted)
• Flash Point: 333.2°C
• PSA: 197.17000
• Density: 2.18g/cm³
• LogP: -2.72460

Purity/Quality:

99%, ^*data from raw suppliers

Vicine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Vicine is a pyrimidine glycosides, a precursor of the aglycons divicine and isouramil which is main factors of favism. It is found in faba/fava bean. Also, it is derived from Ethyl Glyoxylate (E918550), which is used as a reagent in the synthesis of a new class of cinnamyl-triazole compounds which can be used as selective inhibitors of human aromatase (cytochrome P 450 19A1)

Technology Process of 2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one

There total 3 articles about 2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one 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: 90.0%

guanidine nitrate (113-00-8) + ethyl 2-cyano-2-acetate → vicine (152-93-2)

Guidance literature:

In ethanol; for 3h; Ambient temperature;

Reference yield: 30.0%

tetrabenzylvicine → vicine (152-93-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 72h;

Reference yield:

ethyl (R)-2-cyano-2-acetate (160812-25-9) → vicine (152-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOEt / ethanol; CH₂Cl₂ / 1 h / Heating

2: 30 percent / H₂ / 10percent Pd/C / acetic acid / 72 h

With hydrogen; sodium ethanolate; palladium on activated charcoal; In ethanol; dichloromethane; acetic acid;

upstream raw materials:

guanidine nitrate

ethyl (R)-2-cyano-2-acetate

Refernces