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

Base Information

• Chemical Name: N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine
• CAS No.: 292642-58-1
• Molecular Formula: C₃₁H₄₂IN₅O₅Si₂
• Molecular Weight: 747.78

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

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

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

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

triethylsilyl chloride (994-30-9) + N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine (292642-56-9) → N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine (292642-58-1)

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-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine (292642-58-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / imidazole / dimethylformamide / 10 h / 25 °C

2.1: 91 percent / (i-Pr)2NH; BuLi; I₂ / tetrahydrofuran; hexane

3.1: 94 percent / TBAF*3H₂O / tetrahydrofuran / 10 h

4.1: DCC; Cl₂CHCOOH / dimethylsulfoxide

4.2: 19 percent / EtMgBr / tetrahydrofuran / 0.5 h / 25 °C

5.1: 335.5 mg / imidazole / dimethylformamide / 12 h / 25 °C

With 1H-imidazole; dichloro-acetic acid; n-butyllithium; tetrabutyl ammonium fluoride; iodine; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Iodination / 3.1: desilylation / 4.1: Substitution / 4.2: Alkylation / 5.1: Etherification;

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

Reference yield:

N6-benzoyl-8-iodo-2',3'-O-isopropylideneadenosine (292642-47-8) → N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-5-O-(triethylsilyl)-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine (292642-58-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DCC; Cl₂CHCOOH / dimethylsulfoxide

1.2: 19 percent / EtMgBr / tetrahydrofuran / 0.5 h / 25 °C

2.1: 335.5 mg / imidazole / dimethylformamide / 12 h / 25 °C

With 1H-imidazole; dichloro-acetic acid; dicyclohexyl-carbodiimide; In dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Alkylation / 2.1: Etherification;

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

upstream raw materials:

triethylsilyl chloride

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

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

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

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