2'-deoxyaristeromycin

Base Information

• Chemical Name: 2'-deoxyaristeromycin
• CAS No.: 57345-51-4
• Molecular Formula: C11H15 N5 O2
• Molecular Weight: 249.27
• Mol file: 57345-51-4.mol

Synonyms:Cyclopentanemethanol,4-(6-amino-9H-purin-9-yl)-2-hydroxy-, [1R-(1a,2b,4a)]-; 2'-Deoxyaristeromycin

Chemical Property of 2'-deoxyaristeromycin

Chemical Property:

• Vapor Pressure: 9.83E-14mmHg at 25°C
• Boiling Point: 567.9°Cat760mmHg
• Flash Point: 297.2°C
• PSA: 110.08000
• Density: 1.77g/cm³
• LogP: 0.29400

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-deoxyaristeromycin

There total 28 articles about 2'-deoxyaristeromycin 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: 89.0%

(1R,2R,4R)-4-(9H-adenin-9-yl)-2-(hydroxymethyl)cyclopentan-1-ol hydrochloride → (1S,2R,4R)-4-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentan-1-ol (57345-51-4)

Guidance literature:

With amberlite IRA 93; In methanol;

DOI:10.1002/hlca.19940770608

Reference yield:

→ (+/-)-9-<4trans-Hydroxy-3cis-hydroxymethyl-cyclopentyl-(ref)>-adenin (23722-91-0,57345-51-4,137490-73-4,149884-38-8)

Guidance literature:

(+-)-6-Chlor-9-<4trans-Hydroxy-3cis-hydroxymethyl-cyclopentyl-(ref)>-9H-purin, NH3;

DOI:10.1016/S0040-4039(01)88129-6

Reference yield:

4,6-dichloro-5-formamidopyrimidine (123240-66-4) + (+)-(1S, 2R, 4R)-4-amino-2-(hydroxymethyl)-1-cyclopentanol (100018-56-2) → (1S,2R,4R)-4-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentan-1-ol (57345-51-4)

Guidance literature:

4,6-dichloro-5-formamidopyrimidine; (+)-(1S, 2R, 4R)-4-amino-2-(hydroxymethyl)-1-cyclopentanol; With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 140 ℃; for 16h;

With ammonium hydroxide; In 1,4-dioxane; at 60 ℃; for 15h;

upstream raw materials:

(1R,2S,4R)-4-(5-amino-6-chloro-4-pyrimidinylamino)-2-hydroxymethylcyclopentane

orthoformic acid triethyl ester

cis-4-cyclopentene-1,3-diol

(1S,3S,4R)-1-O-acetyl-4-<(triphenylmethoxy)methyl>cyclopentane-r-1,c-3-diol

Downstream raw materials:

8-(Benzyloxy)-2'-deoxyaristeromycin

5'-O-DMT-8-oxo-7,8-dihydro-2'-deoxycarbainosine

N-(9-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-9H-purin-6-yl)benzamide

Refernces

Stereospecific synthesis of (+)-carbocyclic 2'-deoxyadenosine. An improved procedure for the preparation of (+)-(1R,2S,)-4-amino-2-hydroxy-1-hydroxymethylcyclopentane

10.1016/S0040-4020(01)89811-2

This study presents an improved method for the synthesis of (+)-carbocyclic 2'-deoxyadenosine, a nucleoside analog with potential antiviral properties, starting from the bicyclic lactone diol (+)-1. The key steps involve the sequential iodide decarboxylation of the carboxylic acid side chain derived from the lactone moiety of (+)-1 using iodobenzene diacetate (IBDA) and a hypervalent iodine species. The tetrahydropyranyl (THP) group was used for protection, replacing the secondary mesyloxy functionality with an azide anion, while a complete inversion of the configuration was performed. The heterocyclic moiety (adenine) was constructed by a modified literature method involving the reduction of NO2 to NH2 groups with SnCl2. The study also reports an unexpected formation of a disubstituted 2-oxabicyclo[2.2.1]heptane skeleton formed via a hypervalent iodine species derived from the intermediate. The overall yield and purity of the final product were improved, highlighting the efficiency of the synthetic route and the importance of the reagents and conditions used.

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