9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine

Base Information

• Chemical Name: 9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine
• CAS No.: 1301628-60-3
• Molecular Formula: C₄₄H₄₂N₆O₈
• Molecular Weight: 782.853

Synonyms:9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine

Chemical Property of 9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine

Chemical Property:

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Technology Process of 9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine

There total 2 articles about 9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine 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: 60.0%

C26H30O7 (945382-94-5) + N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) → 9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine (1301628-60-3)

Guidance literature:

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine; With N,O-bis-(trimethylsilyl)-acetamide; In 1,2-dichloro-ethane; at 80 ℃; for 0.5h; Inert atmosphere;

C₂₆H₃₀O₇; With trimethylsulfonium triflate; In toluene; at 80 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo200073q

Reference yield:

4-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (945382-92-3) → 9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine (1301628-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluorormethanesulfonic acid; acetic acid / dichloromethane / 0.5 h / 0 °C

2.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / 80 °C / Inert atmosphere

2.2: 1 h / 80 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; trifluorormethanesulfonic acid; acetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo200073q

Reference yield: 88.0%

9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine (1301628-60-3) → 9-[4-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine (1301628-61-4)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo200073q

upstream raw materials:

4-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

C₂₆H₃₀O₇

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

Downstream raw materials:

9-[4-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine

9-[4-C-allyl-3,5-di-O-benzyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine

(1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-1-benzyloxymethyl-7-benzyloxy-5-methyl-2-oxabicylco[2.2.1]heptane

(1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane

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