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

Base Information

• Chemical Name: 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
• CAS No.: 292642-52-5
• Molecular Formula: C₃₁H₄₂ClN₅O₅Si₂
• Molecular Weight: 656.329

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 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

There total 6 articles about 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 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: 72.0%

triethylsilyl chloride (994-30-9) + 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) → 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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

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

Reference yield:

N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1) → 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)

Guidance literature:

Multi-step reaction with 5 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

5: 72 percent / imidazole / dimethylformamide / 12 h / 25 °C

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 / 5: Etherification;

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-isopropylideneadenosine (292642-45-6) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC; Cl₂CHCOOH; EtMgBr

2: 72 percent / imidazole / dimethylformamide / 12 h / 25 °C

With 1H-imidazole; dichloro-acetic acid; ethylmagnesium bromide; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; 1: Alkylation / 2: Etherification;

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

upstream raw materials:

triethylsilyl chloride

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

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

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

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

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

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