N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}adenine
• CAS No.: 328241-12-9
• Molecular Formula: C₃₆H₄₄N₆O₆Si
• Molecular Weight: 684.867

Synonyms:N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}adenine

Chemical Property of N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}adenine

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Technology Process of N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}adenine

There total 4 articles about N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}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: 95.0%

4-methoxy-benzylamine (2393-23-9) + N6-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine (328241-11-8) → N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}adenine (328241-12-9)

Guidance literature:

In ethanol; at 25 ℃; for 25h;

DOI:10.1002/1522-2675(20001220)83:12<3229::AID-HLCA3229>3.0.CO;2-S

Reference yield:

triethylsilyl chloride (994-30-9) → N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}adenine (328241-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / imidazole / dimethylformamide / 15 h / 25 °C

2: 95 percent / ethanol / 25 h / 25 °C

With 1H-imidazole; In ethanol; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(20001220)83:12<3229::AID-HLCA3229>3.0.CO;2-S

Reference yield:

N6-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine (292642-52-5) → N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-{[(4-methoxyphenyl)methyl]amino}adenine (328241-12-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / TBAF / tetrahydrofuran / 7 h / 25 °C

2: 73 percent / imidazole / dimethylformamide / 15 h / 25 °C

3: 95 percent / ethanol / 25 h / 25 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(20001220)83:12<3229::AID-HLCA3229>3.0.CO;2-S

upstream raw materials:

4-methoxy-benzylamine

N⁶-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine

triethylsilyl chloride

N⁶-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine

Downstream raw materials:

N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7)-8-amino-N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine

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