(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
• CAS No.: 640725-74-2
• Molecular Formula: C11H14ClN5O4
• Molecular Weight: 315.716
• ChEMBL ID: CHEMBL1836701
• DSSTox Substance ID: DTXSID101191370
• Mol file: 640725-74-2.mol

Synonyms:640725-74-2;(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol;2-Amino-6-chloro-9-(2-C-methyl-beta-D-ribofuranosyl)-9H-purine;SCHEMBL790288;CHEMBL1836701;WARIDGHHZMLANX-GITKWUPZSA-N;DTXSID101191370;(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol;6-Chloro-9-(2-C-methyl-beta-D-ribofuranosyl)-9H-purin-2-amine;F12920;A855493;2-amino-6-chloro-9-(2-c-methyl-beta-d-ribofuranosyl)purine;(2R,3R,4R,5R)-2-(2-amino-6-chloropurin-9-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol;(2R,3R,4R,5R)-2-(2-Amino-6-chloro-purin-9-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol

Chemical Property of (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol

Chemical Property:

• Boiling Point: 695.3±65.0 °C(Predicted)
• PKA: 13.11±0.70(Predicted)
• PSA: 139.54000
• Density: 1.99±0.1 g/cm3(Predicted)
• LogP: -0.35530
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 315.0734316
• Heavy Atom Count: 21
• Complexity: 407

Purity/Quality:

97% ^*data from raw suppliers

(2R,3R,4R,5R)-2-(2-Amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(OC1N2C=NC3=C2N=C(N=C3Cl)N)CO)O)O
• Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(N=C3Cl)N)CO)O)O

Technology Process of (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol

There total 3 articles about (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-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: 92.0%

(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate (641571-44-0) → (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol (640725-74-2)

Guidance literature:

With ammonia; In methanol; for 7h;

DOI:10.1021/jm030424e

Reference yield:

2-Amino-6-chloropurin (10310-21-1) → (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol (640725-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylsilyl triflate / acetonitrile / 4 h / 65 °C

2: 92 percent / NH₃ / methanol / 7 h

With trimethylsilyl trifluoromethanesulfonate; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; acetonitrile; 1: Vorbrueggen reaction;

DOI:10.1021/jm030424e

Reference yield:

(2S/R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyltetrahydrofuran-2,3,4-triyltribenzoate → (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol (640725-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylsilyl triflate / acetonitrile / 4 h / 65 °C

2: 92 percent / NH₃ / methanol / 7 h

With trimethylsilyl trifluoromethanesulfonate; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; acetonitrile; 1: Vorbrueggen reaction;

DOI:10.1021/jm030424e

upstream raw materials:

(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

2-Amino-6-chloropurin

Downstream raw materials:

isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

2-(2-amino-6-dimethylamino-9H-purin-9-yl)-5-hydroxymethyl-3-methyltetrahydrofuran-3,4-diol

isopropyl 3-(2-(((((3aR,4R,6R,6aR)-6-(2,6-diamino-9H-purin-9-yI)-6a-methyl-2-oxotetrahydrofuro[3,4-d][1,3]dioxoI-4-yI)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yI)amino)phosphoryl)oxy)phenyl)propanoate

isopropyl 3-(2-(((((3aR,4R,6R,6aR)-6-(2,6-diamino-9H-purin-9-yI)-6a-methyl-2-oxotetrahydrofuro[3,4-d][1,3]dioxoI-4-yI)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yI)amino)phosphoryl)oxy)phenyl)propanoate