(1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Base Information

• Chemical Name: (1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS No.: 58462-31-0
• Molecular Formula: C₁₁H₁₃ClN₄O₃
• Molecular Weight: 284.702

Synonyms:(1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Chemical Property of (1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

There total 2 articles about (1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol 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: 64.0%

(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride (79200-57-0) + 4,6-dichloro-5-formamidopyrimidine (123240-66-4) → (1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol (58462-31-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; water; at 120 ℃; for 6h; Microwave irradiation; Sealed tube;

DOI:10.1021/acs.orglett.1c03936

Reference yield:

(+/-)-(1RS,2SR,3RS,5RS)-3-(5-amino-6-chloro-pyrimidin-4-yl-amino)-5-hydroxymethyl-cyclopentane-1,2-diol (13190-82-4,49815-22-7,62413-50-7,72345-99-4,78738-51-9,91382-83-1,122088-66-8,123880-27-3) + orthoformic acid triethyl ester (122-51-0) → (+/-)-9-<β-(2α,3α-dihydroxy-4β-(hydroxymethyl)cyclopentyl)>-6-chloropurine (49815-23-8,58462-31-0,62357-69-1,69979-45-9,120330-85-0)

Guidance literature:

With hydrogenchloride; for 12h;

DOI:10.1016/0040-4020(95)00246-5

Reference yield: 12.77%

(1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol (58462-31-0) + 1-(1,1′-biphenyl-4-yl)piperazine (180698-19-5) → (1R,2S,3R,5R)-3-(6-(4-([1,1'-biphenyl]-4-yl)piperazin-1-yl)-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; at 70 ℃; for 17h;

DOI:10.1021/acs.jmedchem.9b00020

upstream raw materials:

(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride

4,6-dichloro-5-formamidopyrimidine

(+/-)-(1RS,2SR,3RS,5RS)-3-(5-amino-6-chloro-pyrimidin-4-yl-amino)-5-hydroxymethyl-cyclopentane-1,2-diol

orthoformic acid triethyl ester

Downstream raw materials:

aristeromycin

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