N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-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-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine
• CAS No.: 292642-56-9
• Molecular Formula: C₂₅H₂₈IN₅O₅Si
• Molecular Weight: 633.518

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

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

Chemical Property:

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

There total 5 articles about N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-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: 88.0%

N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine (244263-89-6) → N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine (292642-56-9)

Guidance literature:

With N-iodo-succinimide; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; acetic acid; at -78 - 23 ℃;

DOI:10.1002/hlca.200490269

Reference yield: 19.0%

N6-benzoyl-8-iodo-2',3'-O-isopropylideneadenosine (292642-47-8) + trimethylsilylacetylene (1066-54-2) → 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-7-C-(trimethylsilyl)-α-L-talo-hept-6-ynofuranosyl]-8-iodoadenine (292642-57-0)

Guidance literature:

N⁶-benzoyl-8-iodo-2',3'-O-isopropylideneadenosine; With dichloro-acetic acid; dicyclohexyl-carbodiimide; In dimethyl sulfoxide;

trimethylsilylacetylene; With ethylmagnesium bromide; In tetrahydrofuran; at 25 ℃; for 0.5h;

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-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine (292642-56-9)

Guidance literature:

Multi-step reaction with 4 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

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;

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

upstream raw materials:

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

trimethylsilylacetylene

N⁶-benzoyl-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

Downstream raw materials:

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

C₆₅H₈₈N₁₀O₁₀Si₃

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

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