3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

Base Information

• Chemical Name: 3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
• CAS No.: 125073-27-0
• Molecular Formula: C₁₁H₁₆N₆O₃
• Molecular Weight: 280.286
• Mol file: 125073-27-0.mol

Synonyms:1,2-Cyclopentanediol,3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-, (1a,2a,3a,5a)- (9CI); 1,2-Cyclopentanediol,3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-, (1a,2a,3a,5a)-(?à)-

Chemical Property of 3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

Chemical Property:

• Vapor Pressure: 7.31E-21mmHg at 25°C
• Boiling Point: 705°C at 760 mmHg
• Flash Point: 380.2°C
• PSA: 157.06000
• Density: 2.08g/cm³
• LogP: -1.22290

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

There total 7 articles about 3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol 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: 51.7%

(+/-)-(1α,2α,3α,5α)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (125073-25-8,75797-17-0) → (+/-)-(1α,2α,3α,5α)-3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (125073-27-0)

Guidance literature:

With ammonia; In methanol; at 75 ℃; for 57h;

DOI:10.1021/jm00166a020

Reference yield:

(1α,2α,3β,5β)-(+/-)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (88852-57-7,75797-17-0) → (1α,2α,3β,5β)-(+/-)-3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (75797-18-1,88852-58-8,108742-10-5,125073-27-0)

Guidance literature:

With ammonia; at 80 ℃; for 20h;

DOI:10.1021/jm00371a020

Reference yield:

(1S,2R,3S,5S)-3-(2,5-Diamino-6-chloro-pyrimidin-4-ylamino)-5-hydroxymethyl-cyclopentane-1,2-diol (50619-39-1) → (1α,2α,3β,5β)-(+/-)-3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (75797-18-1,88852-58-8,108742-10-5,125073-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / 12 N aq. HCl / N,N-dimethyl-acetamide / 20 h / Ambient temperature

2: liquid NH₃ / 20 h / 80 °C

With hydrogenchloride; ammonia; In N,N-dimethyl acetamide;

DOI:10.1021/jm00371a020

upstream raw materials:

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

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

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

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

Refernces

• 1、 Shealy,Clayton,Arnett,Shannon. "Synthesis and antiviral evaluation of carbocyclic analogues of ribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines". . p. 670 - 674. Retrieved 2007/10/02.