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

Base Information

• Chemical Name: N⁶-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine
• CAS No.: 292642-48-9
• Molecular Formula: C₂₅H₂₈ClN₅O₅Si
• Molecular Weight: 542.066

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

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

There total 4 articles about N⁶-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-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:

N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1) → N6-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine (292642-48-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / imidazole / dimethylformamide / 10 h / 25 °C

2: 97 percent / (i-Pr)2NH; BuLi; PhSO₂Cl / tetrahydrofuran; hexane / -78 °C

3: 100 percent / TBAF / tetrahydrofuran / 15 h

4: DCC; Cl₂CHCOOH; EtMgBr

With 1H-imidazole; dichloro-acetic acid; n-butyllithium; ethylmagnesium bromide; tetrabutyl ammonium fluoride; diisopropylamine; benzenesulfonyl chloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1: Etherification / 2: Chlorination / 3: desilylation / 4: Alkylation;

DOI:10.1002/1522-2675(20000705)83:7<1331::AID-HLCA1331>3.0.CO;2-Z

Reference yield:

N6-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine (292642-43-4) → N6-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine (292642-48-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / (i-Pr)2NH; BuLi; PhSO₂Cl / tetrahydrofuran; hexane / -78 °C

2: 100 percent / TBAF / tetrahydrofuran / 15 h

3: DCC; Cl₂CHCOOH; EtMgBr

With dichloro-acetic acid; n-butyllithium; ethylmagnesium bromide; tetrabutyl ammonium fluoride; diisopropylamine; benzenesulfonyl chloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; 1: Chlorination / 2: desilylation / 3: Alkylation;

DOI:10.1002/1522-2675(20000705)83:7<1331::AID-HLCA1331>3.0.CO;2-Z

Reference yield:

N6-benzoyl-8-chloro-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine (292642-44-5) → N6-benzoyl-8-chloro-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine (292642-48-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / TBAF / tetrahydrofuran / 15 h

2: DCC; Cl₂CHCOOH; EtMgBr

With dichloro-acetic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1: desilylation / 2: Alkylation;

DOI:10.1002/1522-2675(20000705)83:7<1331::AID-HLCA1331>3.0.CO;2-Z

upstream raw materials:

N⁶-benzoyl-8-chloro-2',3'-O-isopropylideneadenosine

trimethylsilylacetylene

N-6-benzoyl-2',3'-O-isopropylideneadenosine

N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine

Downstream raw materials:

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

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