9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N⁶,N⁶-dimethyladenine

Base Information

• Chemical Name: 9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N⁶,N⁶-dimethyladenine
• CAS No.: 934011-52-6
• Molecular Formula: C₂₀H₂₂N₆O₆S
• Molecular Weight: 474.497

Synonyms:9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N⁶,N⁶-dimethyladenine

Chemical Property of 9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N⁶,N⁶-dimethyladenine

Chemical Property:

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Technology Process of 9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N⁶,N⁶-dimethyladenine

There total 2 articles about 9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N⁶,N⁶-dimethyladenine 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: 98.5%

benzyl isothiocyanate (3173-56-6) + 9-(3,5-O-sulfinyl-β-D-xylofuranosyl)-N6,N6-dimethyladenine (669055-54-3) → 9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N6,N6-dimethyladenine (934011-52-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; acetonitrile; at 25 ℃; for 21h;

DOI:10.1080/15257770600725929

Reference yield:

9-(β-D-xylofuranosyl)-N6,N6-dimethyladenine (669055-52-1) → 9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N6,N6-dimethyladenine (934011-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / thionyl chloride; pyridine / acetonitrile / 8 h / 25 °C

2: 98.5 percent / Et₃N / tetrahydrofuran; acetonitrile / 21 h / 25 °C

With pyridine; thionyl chloride; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1080/15257770600725929

Reference yield:

9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N6,N6-dimethyladenine (934011-52-6) → 3'-amino-3'-deoxy-N6,N6-dimethyladenosine (58-60-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH; dipotassium hydrogenphosphate / dimethylformamide / 20 h / -30 °C

2: 70.3 percent / aq. NaOH / various solvent(s) / 96 h / 20 °C

3: 71.4 percent / NH₄HCO₂ / Pd(OH)2-C / H₂O; methanol / 13 h / Heating

With sodium hydroxide; dipotassium hydrogenphosphate; ammonium formate; sodium hydride; palladium hydroxide - carbon; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1080/15257770600725929

upstream raw materials:

benzyl isothiocyanate

9-(3,5-O-sulfinyl-β-D-xylofuranosyl)-N⁶,N⁶-dimethyladenine

9-(β-D-xylofuranosyl)-N⁶,N⁶-dimethyladenine

Downstream raw materials:

9-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]-N⁶,N⁶-dimethyladenine

4-benzylamino-2-(6-dimethylamino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol

3'-amino-3'-deoxy-N⁶,N⁶-dimethyladenosine

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