Griseolic acid

Base Information

• Chemical Name: Griseolic acid
• CAS No.: 79030-08-3
• Molecular Formula: C₁₄H₁₃N₅O₈
• Molecular Weight: 379.286
• UNII: JL8ZD6U3JA
• DSSTox Substance ID: DTXSID701000208
• Wikidata: Q82993645
• Mol file: 79030-08-3.mol

Synonyms:griseolic acid

Chemical Property of Griseolic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.7000 (estimate)
• Boiling Point: 953.3°C at 760 mmHg
• Flash Point: 530.3°C
• PSA: 203.14000
• Density: 2.26g/cm³
• LogP: -1.56900
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 379.07641239
• Heavy Atom Count: 27
• Complexity: 690

Purity/Quality:

99% ^*data from raw suppliers

GRISEOLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OC1(C(C(=O)O)O)C(=O)O

Technology Process of Griseolic acid

There total 4 articles about Griseolic acid 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:

(5R,6R,6aS)-5-(6-Amino-purin-9-yl)-2-((R)-benzhydryloxycarbonyl-hydroxy-methyl)-6-benzoyloxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid benzhydryl ester (98871-19-3) → S-7'-hydroxy-7'-deoxygriseolic acid (79030-08-3,99146-56-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 79.5 percent / 4-(dimethylamino)pyridine, phosphorous pentoxide / CH₂Cl₂ / 2 h / protection from moisture

2: 2.) 1 N hydrochloric acid / 1.) acetic acid, 1 h, 95 deg C, protection from moisture; 2.) 90 percent (v/v) aqueous acetone, pH < 1, r.t., 1 h

3: anisole, trifluoroacetic acid

4: 20 percent (v/v) ammonia / methanol

With hydrogenchloride; dmap; phosphorus pentaoxide; ammonia; methoxybenzene; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1248/cpb.35.4442

Reference yield:

dibenzhydryl O2'-benzoyl-S-7'-acetoxy-7'-deoxygriseolate (98890-08-5) → S-7'-hydroxy-7'-deoxygriseolic acid (79030-08-3,99146-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: anisole, trifluoroacetic acid

2: 20 percent (v/v) ammonia / methanol

With ammonia; methoxybenzene; trifluoroacetic acid; In methanol;

DOI:10.1248/cpb.35.4442

Reference yield:

dibenzhydryl O2'-benzoyl-O7'-trifluoromathanesulfonylgriseolate (98889-87-3) → S-7'-hydroxy-7'-deoxygriseolic acid (79030-08-3,99146-56-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) 1 N hydrochloric acid / 1.) acetic acid, 1 h, 95 deg C, protection from moisture; 2.) 90 percent (v/v) aqueous acetone, pH < 1, r.t., 1 h

2: anisole, trifluoroacetic acid

3: 20 percent (v/v) ammonia / methanol

With hydrogenchloride; ammonia; methoxybenzene; trifluoroacetic acid; In methanol;

DOI:10.1248/cpb.35.4442

upstream raw materials:

(5R,6R,6aS)-2-((S)-Acetoxy-carboxy-methyl)-5-(6-amino-purin-9-yl)-6-benzoyloxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid

(5R,6R,6aS)-5-(6-Amino-purin-9-yl)-2-((R)-benzhydryloxycarbonyl-hydroxy-methyl)-6-benzoyloxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid benzhydryl ester

dibenzhydryl O^2'-benzoyl-S-7'-acetoxy-7'-deoxygriseolate

dibenzhydryl O^2'-benzoyl-O^7'-trifluoromathanesulfonylgriseolate

Downstream raw materials:

dibenzhydryl N⁶,N⁶,O^2',O^7'-tetrabenzoylgriseolate

N⁶,O^2',O^7'-tribenzoylgriseolic acid, disodium salt

dibenzhydryl O^2',O^7'-dibenzoylgriseolate

dibenzhydryl N⁶,O^2',O^7'-triacetylgriseolate

Refernces