Pentanoic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Pentanoic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester
• CAS No.: 87970-07-8
• Molecular Formula: C₁₅H₂₁N₅O₅
• Molecular Weight: 351.362
• DSSTox Substance ID: DTXSID601007887
• Wikidata: Q83004158
• Mol file: 87970-07-8.mol

Synonyms:87970-07-8;Pentanoic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester;DTXSID601007887;9-(2-O-Pentanoylpentofuranosyl)-9H-purin-6-amine;[(2R,3S,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] pentanoate

Chemical Property of Pentanoic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Chemical Property:

• Vapor Pressure: 1.07E-16mmHg at 25°C
• Boiling Point: 629.2°C at 760 mmHg
• Flash Point: 334.3°C
• Density: 1.64g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 351.15426879
• Heavy Atom Count: 25
• Complexity: 470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(=O)OC1C(C(OC1N2C=NC3=C(N=CN=C32)N)CO)O
• Isomeric SMILES: CCCCC(=O)O[C@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O

Technology Process of Pentanoic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

There total 4 articles about Pentanoic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester 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: 86.0%

9-<2-O-valeryl-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine (87984-85-8) → 9-(2-O-valeryl-β-D-arabinofuranosyl)adenine (87970-07-8)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1021/jm00369a007

Reference yield:

pentanoic anhydride (2082-59-9) → 9-(2-O-valeryl-β-D-arabinofuranosyl)adenine (87970-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / 48 h / 0 - 5 °C

2: 86 percent / n-Bu₄NF, glacial AcOH / tetrahydrofuran

With pyridine; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1021/jm00369a007

Reference yield:

9-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine (82870-42-6) → 9-(2-O-valeryl-β-D-arabinofuranosyl)adenine (87970-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / 48 h / 0 - 5 °C

2: 86 percent / n-Bu₄NF, glacial AcOH / tetrahydrofuran

With pyridine; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1021/jm00369a007

upstream raw materials:

9-<2-O-valeryl-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine

pentanoic anhydride

9-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine

arabinosyl adenine