1-(6-Amino-9h-purin-9-yl)-2,5-anhydro-1-deoxyhexitol

Base Information

• Chemical Name: 1-(6-Amino-9h-purin-9-yl)-2,5-anhydro-1-deoxyhexitol
• CAS No.: 29868-39-1
• Molecular Formula: C11H15 N5 O4
• Molecular Weight: 281.271
• NSC Number: 133720
• DSSTox Substance ID: DTXSID50299927
• Mol file: 29868-39-1.mol

Synonyms:29868-39-1;1-(6-amino-9h-purin-9-yl)-2,5-anhydro-1-deoxyhexitol;NSC133720;DTXSID50299927;NSC-133720

Chemical Property of 1-(6-Amino-9h-purin-9-yl)-2,5-anhydro-1-deoxyhexitol

Chemical Property:

• Vapor Pressure: 4.71E-18mmHg at 25°C
• Boiling Point: 655.1°Cat760mmHg
• Flash Point: 350°C
• PSA: 139.54000
• Density: 1.94g/cm³
• LogP: -1.52880
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 281.11240398
• Heavy Atom Count: 20
• Complexity: 349

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)CC3C(C(C(O3)CO)O)O)N

Technology Process of 1-(6-Amino-9h-purin-9-yl)-2,5-anhydro-1-deoxyhexitol

There total 13 articles about 1-(6-Amino-9h-purin-9-yl)-2,5-anhydro-1-deoxyhexitol 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: 67.0%

9-(((3aS,4S,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-9H-purin-6-amine (1345992-93-9) → XZ-150-129-A (29868-39-1)

Guidance literature:

9-(((3aS,4S,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-9H-purin-6-amine; With methanol; acetyl chloride; at 20 ℃; for 7.5h;

With sodium methylate; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.tetlet.2011.09.074

Reference yield:

1-deoxy-1-methoxycarbonyl-5-O-tert-butyldiphenylsilyl-2,3-O-isopropyridene-β-D-ribofuranose → XZ-150-129-A (29868-39-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: diisobutylaluminium hydride / dichloromethane / 24 h / -78 - 20 °C

2.1: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C

3.1: potassium tert-butylate / tetrahydrofuran / 2 h / 20 °C

4.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 4 h / 20 °C

5.1: sodium periodate; periodic acid / ethyl acetate / 3 h / 20 °C

6.1: sodium tetrahydroborate / ethyl acetate / 20 °C / Cooling with ice

7.1: dmap; triethylamine / dichloromethane / 4 h / Reflux

8.1: lithium hydride / dimethyl sulfoxide / 0.5 h / 90 °C / Inert atmosphere

8.2: 4 h / 90 °C / Inert atmosphere

9.1: methanol; acetyl chloride / 7.5 h / 20 °C

9.2: 0.08 h / 20 °C

With methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; potassium tert-butylate; water; lithium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; periodic acid; triethylamine; acetyl chloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetone;

DOI:10.1016/j.tetlet.2011.09.074

Reference yield:

C26H36O5Si (1345992-82-6) → XZ-150-129-A (29868-39-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 2 h / 20 °C

3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 4 h / 20 °C

4.1: sodium periodate; periodic acid / ethyl acetate / 3 h / 20 °C

5.1: sodium tetrahydroborate / ethyl acetate / 20 °C / Cooling with ice

6.1: dmap; triethylamine / dichloromethane / 4 h / Reflux

7.1: lithium hydride / dimethyl sulfoxide / 0.5 h / 90 °C / Inert atmosphere

7.2: 4 h / 90 °C / Inert atmosphere

8.1: methanol; acetyl chloride / 7.5 h / 20 °C

8.2: 0.08 h / 20 °C

With methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; potassium tert-butylate; water; lithium hydride; 4-methylmorpholine N-oxide; periodic acid; triethylamine; acetyl chloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetone;

DOI:10.1016/j.tetlet.2011.09.074

upstream raw materials:

C₂₆H₃₆O₅Si

C₂₇H₃₈O₇SSi

C₂₆H₃₄O₄Si

C₂₆H₃₆O₆Si

Downstream raw materials:

9-N-[(2',3'-O-diacetyl-β-D-ribo-pentofuranosyl)methyl]-N⁶-benzoyladenine

9-N-[(2'-O-(tetrahydrofuranyl)-β-D-ribo-pentafuranosyl)methyl]-N⁶-benzoyladenine

9-N-[(3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentafuranosyl)methyl]-N⁶-benzoyladenine

9-N-[(5'-O-(4,4'-dimethoxytrityl)-β-D-ribo-pentafuranosyl)methyl]-N⁶-benzoyladenine