{(2S,5R)-5-[6-(hexyloxy)-9H-purin-9-yl]tetrahydrofuran-2-yl}methanol

Base Information

• Chemical Name: {(2S,5R)-5-[6-(hexyloxy)-9H-purin-9-yl]tetrahydrofuran-2-yl}methanol
• CAS No.: 146202-53-1
• Molecular Formula: C₁₆H₂₄N₄O₃
• Molecular Weight: 320.392
• Mol file: 146202-53-1.mol

Synonyms:6-Hexoxy-PddN deriv.;6-Hexopurine-2',3'-dideoxynucleoside;Inosine,2',3'-dideoxy-6-O-hexyl;

Chemical Property of {(2S,5R)-5-[6-(hexyloxy)-9H-purin-9-yl]tetrahydrofuran-2-yl}methanol

Chemical Property:

• Vapor Pressure: 1.27E-11mmHg at 25°C
• Boiling Point: 519.6°Cat760mmHg
• Flash Point: 268°C
• PSA: 82.29000
• Density: 1.34g/cm³
• LogP: 2.45530

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2S,5R)-5-[6-(hexyloxy)-9H-purin-9-yl]tetrahydrofuran-2-yl}methanol

There total 4 articles about {(2S,5R)-5-[6-(hexyloxy)-9H-purin-9-yl]tetrahydrofuran-2-yl}methanol 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: 34.0%

3'-Deoxythymidine (3416-05-5) + 6-(6-hexyloxy)-9H-purine (62134-31-0) → 6-(hexyloxy)-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine (146202-53-1)

Guidance literature:

With 4-nitro-phenol; potassium phosphate buffer containing 0.004percent potassium azide (buffer A); TPase; at 35 ℃; for 7.5h;

DOI:10.1021/jm00055a009

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 6-(hexyloxy)-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine (146202-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92.8 percent / H₂ / 5percent Pd/C / dioxane / 760 Torr

2: 34 percent / 10mM potassium phosphate buffer containing 0.004percent potassium azide (buffer A), PNP, TPase / 7.5 h / 35 °C

With 4-nitro-phenol; potassium phosphate buffer containing 0.004percent potassium azide (buffer A); TPase; hydrogen; palladium on activated charcoal; In 1,4-dioxane;

DOI:10.1021/jm00055a009

Reference yield:

hexan-1-ol (111-27-3) → 6-(hexyloxy)-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine (146202-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.54 g / NaOH / tetrahydrofuran

2: 34 percent / 10mM potassium phosphate buffer containing 0.004percent potassium azide (buffer A), PNP, TPase / 7.5 h / 35 °C

With sodium hydroxide; 4-nitro-phenol; potassium phosphate buffer containing 0.004percent potassium azide (buffer A); TPase; In tetrahydrofuran;

DOI:10.1021/jm00055a009

upstream raw materials:

3'-Deoxythymidine

6-(6-hexyloxy)-9H-purine

(S)-2-<(benzoyloxy)methyl>cyclobutanone

thymidine

Refernces

• 1、 Lee-Ruff, Edward,Xi, Feng-De,Qie, Jiang Hua. "Enantioselective preparation of 2′,3′-dideoxynucleosides and their analogues from ring-expansion of cyclobutanones. 2. Synthesis of 2′,3′-dideoxyribosides and (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane". . p. 1547 - 1550. Retrieved 2007/10/03.