194034-59-8

Basic information

• Product Name: 2-AMino-6-chloropurine-9-(2'-O-Methyl)riboside
• Synonyms: 2-AMino-6-chloropurine-9-(2'-O-Methyl)riboside;2-AMino-6-chloro-9-(2'-O -Methyl-beta-D-ribofuranosyl)-9H-purine;6-chloro-9-(2-O-Methyl-beta-D-ribofuranosyl)-9H-purin-2-aMine
• CAS NO: 194034-59-8
• Molecular Formula: C11H14ClN5O4
• Molecular Weight: 315.71296
• Mol File: 194034-59-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-AMino-6-chloropurine-9-(2'-O-Methyl)riboside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMino-6-chloropurine-9-(2'-O-Methyl)riboside(194034-59-8)
• EPA Substance Registry System: 2-AMino-6-chloropurine-9-(2'-O-Methyl)riboside(194034-59-8)

Safety Data

• Hazardous Substances Data: 194034-59-8(Hazardous Substances Data)

Usage

Classification

Purine nucleoside

Derivative of

Adenine

Common Use

Scientific research and pharmaceutical development

Application

Precursor for synthesis of nucleoside analogs

Therapeutic Potential

Treatment of viral infections and cancer

Chemical Modifications

Addition of chloro group and methyl group

Biochemical Properties Enhancement

Result of chemical modifications

Stability Improvement

Likely due to chemical modifications

Bioavailability Enhancement

Likely due to chemical modifications

Significance

Important chemical tool

Promising Applications

Basic research and medical science

Upstream product

• 2004-07-1 2-Amino-6-chloropurine riboside 
• 74-88-4 methyl iodide 

Downstream Products

• 2140-71-8 2'-O-methylguanosine 
• 2140-79-6 2'-O-methyl adenosine 

Relevant articles and documents

Improved synthetic approaches toward 2'-O-methyl-adenosine and guanosine and their N-acyl derivatives

We developed several improved approaches toward 2'-O-methyl adenosine and guanosine and their N-acyl derivatives. (a) Transglycosylation of N4- acetyl-5', 3'-di-O-acetyl-2'-O-methyl cytidine with N6-Bz-adenine provided N6-benzoyl-5'3'-di-O-acetyl-2'-O-methyl adenosine in 50% yield. (b) Regioselective methylation of 2-amino-6-chloro purine riboside with MeI/NaH followed by hydrolysis provided 2'-O-Me-guanosine in high yield. The same 2'- O-Me-precursor was transformed into 2'-O-Me-adenosine in 58% yield. (c) Very efficient transformation of 2,6-diamino-purine riboside into N2-isobutyryl (isopropylphenoxyacetyl) 2'-O-Me-guanosine through methylation of 5',3'-O- TIPDSi derivative followed by selective N2-acylation, deamination and desylilation provided target compounds in 70% combined yield. (d) Mg2+ and Ag+ directed methylation of N1-Bzl-guanosine proceeded in >80% yield with ratio of 2'-O-Me-3'-O-Me=9:1. The same methylation of adenosine with Ag+ and Sr2+ acetylacetonates provided 2'-O-Me-adenosine in 75-80% yield. (C) 2000 Elsevier Science Ltd.