Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(3-azido-2-phenylselanyl-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(3-azido-2-phenylselanyl-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester
• CAS No.: 216080-68-1
• Molecular Formula: C₂₃H₂₅N₇O₅Se
• Molecular Weight: 558.455
• Mol file: 216080-68-1.mol

Synonyms:

Chemical Property of Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(3-azido-2-phenylselanyl-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(3-azido-2-phenylselanyl-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester

There total 2 articles about Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(3-azido-2-phenylselanyl-propyl)-purin-9-yl]-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: 50.0%

diphenyl diselenide (1666-13-3) + Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-allyl-purin-9-yl)-tetrahydro-furan-3-yl ester (216080-65-8) → Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(3-azido-2-phenylselanyl-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester (216080-68-1)

Guidance literature:

With sodium azide; [bis(acetoxy)iodo]benzene; In dichloromethane;

DOI:10.1080/07328319808004751

Reference yield:

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(toluene-4-sulfonyloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester → Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(3-azido-2-phenylselanyl-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester (216080-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / Pd(PPh₃)4, LiCl / dioxane

2: 50 percent / NaN₃, PhI(OAc)2 / CH₂Cl₂

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; [bis(acetoxy)iodo]benzene; lithium chloride; In 1,4-dioxane; dichloromethane;

DOI:10.1080/07328319808004751

Reference yield:

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(3-azido-2-phenylselanyl-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester (216080-68-1) → 1-{3-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-propyl}-3-phenyl-urea

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) nBu₃SnH, BEt₃ / 1.) benzene

2: 72 percent / NaOMe / methanol

With triethyl borane; tri-n-butyl-tin hydride; sodium methylate; In methanol;

DOI:10.1080/07328319808004751

upstream raw materials:

diphenyl diselenide

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-allyl-purin-9-yl)-tetrahydro-furan-3-yl ester

Downstream raw materials:

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-{6-[3-(3-phenyl-ureido)-propyl]-purin-9-yl}-tetrahydro-furan-3-yl ester