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

Base Information

• Chemical Name: N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine
• CAS No.: 244263-89-6
• Molecular Formula: C₂₅H₂₉N₅O₅Si
• Molecular Weight: 507.621

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

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

There total 3 articles about N⁶-benzoyl-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: 40.0%

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) + ethylmagnesium bromide (925-90-6) + trimethylsilylacetylene (1066-54-2) → 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)-α-L-talo-hept-6-ynofuranosyl]adenine (244263-90-9)

Guidance literature:

ethylmagnesium bromide; trimethylsilylacetylene; In tetrahydrofuran; at 0 - 23 ℃;

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde; In tetrahydrofuran; at -15 - 23 ℃;

DOI:10.1002/hlca.200490269

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]adenine (244263-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC; Cl₂CHCOOH / dimethylsulfoxide / 0.17 h / 25 °C

2: EtMgBr / tetrahydrofuran

With dichloro-acetic acid; ethylmagnesium bromide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dimethyl sulfoxide; 1: Oxidation / 2: Grignard reaction;

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

Reference yield:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde (43077-06-1) + trimethylsilylacetylene (1066-54-2) → 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)-α-L-talo-hept-6-ynofuranosyl]adenine (244263-90-9)

Guidance literature:

With ethylmagnesium bromide; In tetrahydrofuran;

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

upstream raw materials:

6-N-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde

trimethylsilylacetylene

ethylmagnesium bromide

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

Downstream raw materials:

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

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

C₆₅H₈₈N₁₀O₁₀Si₃

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

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