2-amino-9-[(1R,2S,3S,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one

Base Information

• Chemical Name: 2-amino-9-[(1R,2S,3S,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one
• CAS No.: 108742-09-2
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.271
• Mol file: 108742-09-2.mol

Synonyms:6H-Purin-6-one,2-amino-9-[2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-1,9-dihydro-, (1a,2b,3a,4a)- (9CI); 6H-Purin-6-one,2-amino-9-[2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-1,9-dihydro-, (1a,2b,3a,4a)-(?à)-; NSC 615827

Chemical Property of 2-amino-9-[(1R,2S,3S,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one

Chemical Property:

• Vapor Pressure: 1.32E-19mmHg at 25°C
• Boiling Point: 683.3°C at 760 mmHg
• Flash Point: 367°C
• Density: 2.08g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-amino-9-[(1R,2S,3S,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one

There total 5 articles about 2-amino-9-[(1R,2S,3S,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one 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:

(+/-)-(1α,2β,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol (108742-05-8) → (+/-)-2-amino-1,9-dihydro-9-<(1α,2β,3α,5α)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-6H-purin-6-one (108742-09-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium acetate trihydrate, acetic acid / H₂O / Ambient temperature

2: 54 percent / zinc, acetic acid / H₂O; ethanol / 1.5 h / Heating

3: 52 percent / concd. HCl / dimethylformamide / 24 h / Ambient temperature

4: 1 N aq. HCl / 5 h / Heating

With hydrogenchloride; sodium acetate; acetic acid; zinc; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00394a017

Reference yield:

(+/-)-(1α,2β,3α,5α)-3-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidyl>amino>-5-(hydroxymethyl)-1,2-cyclopentanediol (108742-06-9) → (+/-)-2-amino-1,9-dihydro-9-<(1α,2β,3α,5α)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-6H-purin-6-one (108742-09-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / zinc, acetic acid / H₂O; ethanol / 1.5 h / Heating

2: 52 percent / concd. HCl / dimethylformamide / 24 h / Ambient temperature

3: 1 N aq. HCl / 5 h / Heating

With hydrogenchloride; acetic acid; zinc; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00394a017

Reference yield:

(+/-)-(1α,2β,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol (91382-82-0,305384-32-1,780705-82-0) → (+/-)-2-amino-1,9-dihydro-9-<(1α,2β,3α,5α)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-6H-purin-6-one (108742-09-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 40 percent / triethylamine / butan-1-ol; methanol / 48 h / Heating

2: sodium acetate trihydrate, acetic acid / H₂O / Ambient temperature

3: 54 percent / zinc, acetic acid / H₂O; ethanol / 1.5 h / Heating

4: 52 percent / concd. HCl / dimethylformamide / 24 h / Ambient temperature

5: 1 N aq. HCl / 5 h / Heating

With hydrogenchloride; sodium acetate; acetic acid; triethylamine; zinc; In methanol; ethanol; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jm00394a017

upstream raw materials:

(+/-)-(1α,2β,3α,5α)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1α,2β,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1α,2β,3α,5α)-3-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidyl>amino>-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1α,2β,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol