(2R,3S,5R)-5-(6-Amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

Base Information

• Chemical Name: (2R,3S,5R)-5-(6-Amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
• CAS No.: 24757-70-8
• Molecular Formula: C11H15N5O4
• Molecular Weight: 281.271
• Hs Code.: 2934990002
• UNII: EAM4X9P3JV
• DSSTox Substance ID: DTXSID10437626
• Nikkaji Number: J585.324I
• Wikidata: Q82253162
• Metabolomics Workbench ID: 173658
• ChEMBL ID: CHEMBL470889
• Mol file: 24757-70-8.mol

Synonyms:24757-70-8;Adenosine, 2'-deoxy-2-methoxy-;2-Methoxy-2'-deoxyadenosine;(2R,3S,5R)-5-(6-Amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol;EAM4X9P3JV;2'-Deoxy-2-methoxyadenosine;(2R,3S,5R)-5-(6-AMINO-2-METHOXYPURIN-9-YL)-2-(HYDROXYMETHYL)OXOLAN-3-OL;Adenosine, 2'-deoxy-2-methoxy- (8CI,9CI);2'-Deoxyspongosine;UNII-EAM4X9P3JV;Cladribine impurity B [EP];2/'-Deoxy-2-methoxyadenosine;CHEMBL470889;DTXSID10437626;CLADRIBINE IMPURITY B [EP IMPURITY];2-METHOXY-2'-DEOXYADENOSINE [USP IMPURITY];9-(2-Deoxy-beta-D-ribofuranosyl)-2-methoxyadenine;9-(2-DEOXY-.BETA.-D-RIBOFURANOSYL)-2-METHOXYADENINE;2-Methoxy-6-amino-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine;(2R,3S,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol;2-METHOXY-6-AMINO-9-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)PURINE

Chemical Property of (2R,3S,5R)-5-(6-Amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

Chemical Property:

• Boiling Point: 659.1±65.0 °C(Predicted)
• PKA: 13.77±0.60(Predicted)
• PSA: 128.54000
• Density: 1.84±0.1 g/cm3(Predicted)
• LogP: -0.36100
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 281.11240398
• Heavy Atom Count: 20
• Complexity: 349

Purity/Quality:

97% ^*data from raw suppliers

2-Methoxy-2''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC(=C2C(=N1)N(C=N2)C3CC(C(O3)CO)O)N
• Isomeric SMILES: COC1=NC(=C2C(=N1)N(C=N2)[C@H]3C[C@@H]([C@H](O3)CO)O)N
• Uses: 2-Methoxy-2''-deoxyadenosine is an impurity in the synthesis of Cladribine (M262330), a substituted purine nucleoside with antileukemic activity.

Technology Process of (2R,3S,5R)-5-(6-Amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

There total 5 articles about (2R,3S,5R)-5-(6-Amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol 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: 85.0%

methanol (67-56-1) + 2-bromo-2′-deoxyadenosine (89178-21-2) → 2'-deoxyspongosine (24757-70-8)

Guidance literature:

With sodium methylate; for 4h; Heating;

DOI:10.1002/hlca.19950780718

Reference yield: 79.0%

trimethyl phosphite (512-56-1) + 2'-deoxyisoguanosine (106449-56-3) → 2'-deoxyspongosine (24757-70-8) + 2'-deoxydoridosine

Guidance literature:

With sodium hydroxide; In water; at 50 ℃; for 24h;

DOI:10.1002/hlca.19950780718

Reference yield: 64.0%

sodium methylate (124-41-4) + 2-chloro-2'-deoxyadenosine (4291-63-8) → 2'-deoxyspongosine (24757-70-8)

Guidance literature:

In methanol; 1.) 70 deg C, 1.5 h, 2.) r.t., overnight, 3.) 70 deg C, 42 h;

DOI:10.1002/jps.2600830416

upstream raw materials:

methanol

2-bromo-2′-deoxyadenosine

sodium methylate

2-chloro-2'-deoxyadenosine

Downstream raw materials:

2-methoxy-9H-purin-6-amine