2'-Thioadenosine

Base Information

• Chemical Name: 2'-Thioadenosine
• CAS No.: 136904-69-3
• Molecular Formula: C₁₀H₁₃N₅O₃S
• Molecular Weight: 283.311
• DSSTox Substance ID: DTXSID20435431
• Wikidata: Q82250360
• ChEMBL ID: CHEMBL14326
• Mol file: 136904-69-3.mol

Synonyms:2'-Thioadenosine;136904-69-3;CHEMBL14326;(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol;thioadenosine;2/'-Thioadenosine;SCHEMBL2699533;DTXSID20435431;60239-18-1 (non-salt);BDBM50057300;PD138045;J-006937;(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-4-mercapto-tetrahydro-furan-3-ol

Chemical Property of 2'-Thioadenosine

Chemical Property:

• Boiling Point: 668.8±65.0 °C(Predicted)
• PKA: 8.72±0.70(Predicted)
• PSA: 158.11000
• Density: 2.02±0.1 g/cm3(Predicted)
• LogP: -0.46130
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 283.07391047
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

97% ^*data from raw suppliers

2''-Thioadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)S)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)S)N
• Uses: 2''-Thioadenosine, is a useful synthetic intermediate for making a potent and selective erbB-1 (a.k.a. epidermal growth factor receptor) and erbB-2 (a.k.a. neu/her2 growth factor receptor) tyrosine kinase inhibitor.

Technology Process of 2'-Thioadenosine

There total 7 articles about 2'-Thioadenosine 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: 78.0%

2'-S-<9-(4-methoxyphenyl)xanthen-9-yl>-2'-thioadenosine (136904-70-6) → 2'-Thioadenosine (136904-69-3)

Guidance literature:

With pyrrole; In acetic acid; at 70 ℃; for 1h;

DOI:10.1016/0008-6215(92)84167-Q

Reference yield:

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine (69304-45-6) → 2'-Thioadenosine (136904-69-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) CrO₃, pyridine, Ac₂O; 2) aq. NaBH₄ / 1) CH₂Cl₂, 9 min; 2) EtOH, 0 deg C, 30 min

2: 93 percent / pyridine / 16 h / Ambient temperature

3: 81 percent / pyridine / CH₂Cl₂ / 5 h / -15 - 10 °C

4: 1) Et₃N, 2) Et₄NF; 3) NH₃ / 1) DMSO, 32 h; 2) MeCN, room temp., 15 min; 3) MeOH, room temp., 22 h

5: 75 percent / PPh₃ / acetic acid / 2 h / 50 °C

6: 78 percent / pyrrole / acetic acid / 1 h / 70 °C

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; pyrrole; ammonia; acetic anhydride; tetraethylammonium fluoride; triethylamine; triphenylphosphine; In dichloromethane; acetic acid;

DOI:10.1016/0008-6215(92)84167-Q

Reference yield:

9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-β-D-arabinofuranosyl]adenine (87792-02-7) → 2'-Thioadenosine (136904-69-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / pyridine / 16 h / Ambient temperature

2: 81 percent / pyridine / CH₂Cl₂ / 5 h / -15 - 10 °C

3: 1) Et₃N, 2) Et₄NF; 3) NH₃ / 1) DMSO, 32 h; 2) MeCN, room temp., 15 min; 3) MeOH, room temp., 22 h

4: 75 percent / PPh₃ / acetic acid / 2 h / 50 °C

5: 78 percent / pyrrole / acetic acid / 1 h / 70 °C

With pyridine; pyrrole; ammonia; tetraethylammonium fluoride; triethylamine; triphenylphosphine; In dichloromethane; acetic acid;

DOI:10.1016/0008-6215(92)84167-Q

upstream raw materials:

2'-S-<9-(4-methoxyphenyl)xanthen-9-yl>-2'-thioadenosine

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine

9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-β-D-arabinofuranosyl]adenine

2'deoxy-2'-<9-(4-methoxyphenyl)xanthen-9-yldithio>adenosine

Refernces