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

Base Information

• Chemical Name: N⁶-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine
• CAS No.: 328241-11-8
• Molecular Formula: C₂₈H₃₄ClN₅O₅Si
• Molecular Weight: 584.147

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

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

Chemical Property:

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

There total 2 articles about N⁶-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]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: 73.0%

triethylsilyl chloride (994-30-9) + N-{8-chloro-9-[6-(1-hydroxy-prop-2-ynyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-benzamide → 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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 15h;

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-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine (328241-11-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

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

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

upstream raw materials:

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

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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