N⁶-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine
• CAS No.: 252001-13-1
• Molecular Formula: C₅₃H₇₁N₅O₁₀Si₃
• Molecular Weight: 1022.43
• Mol file: 252001-13-1.mol

Synonyms:N⁶-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine

Chemical Property of N⁶-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine

There total 1 articles about N⁶-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine 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: 79.0%

N6-benzoyl-9-[methyl 6,10-anhydro-3,8-O-(tert-butyldimethylsilyl)-2-O-methyl-9-O-(tert-butyldiphenylsilyl)-D-arabino-L-ido-7-undeculofuranuronyl]adenine → N6-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine (252001-13-1)

Guidance literature:

With Burgess Reagent; In toluene; for 1h; Heating;

DOI:10.1021/ja992608h

Reference yield:

N6-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine (252001-13-1) → 6-[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-ylmethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-5-oxo-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; at 20 ℃; for 24h;

DOI:10.1021/ja992608h

Reference yield:

N6-benzoyl-9-[methyl 6,10-anhydro-3,8-di-O-(tert-butyldimethylsilyl)-6-dehydro-5-deoxy-9-O-(tertbutyldiphenylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine (252001-13-1) → herbicidin B (55353-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HCO₂NH₄ / 20 percent Pd/C / methanol / 24 h / 20 °C

2.1: SmI₂ / methanol / 0.25 h / 20 °C

2.2: TBAF / tetrahydrofuran / 0.5 h / 0 °C

With samarium diiodide; ammonium formate; palladium on activated charcoal; In methanol; 1.1: Hydrogenation / 2.1: Cyclization / 2.2: deprotection;

DOI:10.1021/ja992608h

Downstream raw materials:

herbicidin B