1-(N⁶-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose

Base Information

• Chemical Name: 1-(N⁶-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose
• CAS No.: 934497-31-1
• Molecular Formula: C₃₂H₃₅ClN₅O₈P
• Molecular Weight: 684.085

Synonyms:1-(N⁶-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose

Chemical Property of 1-(N⁶-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 1-(N⁶-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose

There total 7 articles about 1-(N⁶-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose 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: 73.0%

1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose (934497-30-0) + N-benzoyladenine (4005-49-6) → 1-(N6-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose (934497-31-1)

Guidance literature:

tin(IV) chloride; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tet.2007.01.032

Reference yield:

(diisopropoxyphosphoryl)methyl trifluoromethanesulfonate (134963-85-2) → 1-(N6-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose (934497-31-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / sodium hydride / tetrahydrofuran; various solvent(s) / -78 - 20 °C

2: 99 percent / NaIO₄; H₅IO₆ / ethyl acetate / 5 h / 20 °C

3: n-BuLi / tetrahydrofuran; hexane / 3 h / 0 °C

4: 460 g / TFA / H₂O / 2 h / 20 °C

5: 86 percent / pyridine / 0 - 20 °C

6: 73 percent / SnCl₄ / acetonitrile / 20 °C

With sodium periodate; n-butyllithium; sodium hydride; periodic acid; trifluoroacetic acid; tin(IV) chloride; In tetrahydrofuran; pyridine; hexane; water; ethyl acetate; acetonitrile; 3: Wittig olefination;

DOI:10.1016/j.tet.2007.01.032

Reference yield:

1,2-O-isopropylidene-3-O-(diisopropylphosphonomethyl)-5-oxo-β-L-arabinose (934497-28-6) → 1-(N6-benzoyladenin-9-yl)-2-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α-L-arabinofuranose (934497-31-1)

Guidance literature:

Multi-step reaction with 4 steps

1: n-BuLi / tetrahydrofuran; hexane / 3 h / 0 °C

2: 460 g / TFA / H₂O / 2 h / 20 °C

3: 86 percent / pyridine / 0 - 20 °C

4: 73 percent / SnCl₄ / acetonitrile / 20 °C

With n-butyllithium; trifluoroacetic acid; tin(IV) chloride; In tetrahydrofuran; pyridine; hexane; water; acetonitrile; 1: Wittig olefination;

DOI:10.1016/j.tet.2007.01.032

upstream raw materials:

1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

N-benzoyladenine

(diisopropoxyphosphoryl)methyl trifluoromethanesulfonate

1,2-O-isopropylidene-3-O-(diisopropylphosphonomethyl)-5-oxo-β-L-arabinose

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