N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine

Base Information

• Chemical Name: N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine
• CAS No.: 390824-35-8
• Molecular Formula: C₃₁H₃₀N₆O₁₀
• Molecular Weight: 646.613

Synonyms:N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine

Chemical Property of N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine

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Technology Process of N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine

There total 8 articles about N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-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: 86.0%

N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) + 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose (144490-03-9) → N2-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine (390824-35-8)

Guidance literature:

With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; In toluene; at 80 ℃; for 3h;

DOI:10.1016/S0040-4020(02)00230-2

Reference yield: 73.0%

1,2,3,5-tetraacetyl-L-ribofuranose (176299-71-1) + N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) → N2-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine (390824-35-8)

Guidance literature:

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine; With N,O-bis-(trimethylsilyl)-acetamide; In 1,2-dichloro-ethane; at 80 ℃; for 0.25h;

1,2,3,5-tetraacetyl-L-ribofuranose; With trimethylsilyl trifluoromethanesulfonate; In toluene; at 80 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.7b02988

Reference yield:

methyl 3-O-benzyl-β-L-ribofuranoside (390824-26-7) → N2-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine (390824-35-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / H₂ / 10 percent Pd/C / methanol / 2 h / 20 °C

2: 98 percent / pyridine / 20 °C

3: 77 percent / H₂SO₄ / acetic acid / 4 °C

4: 86 percent / BSA; TMSOTf / toluene / 3 h / 80 °C

With pyridine; benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen; palladium on activated charcoal; In methanol; acetic acid; toluene;

DOI:10.1016/S0040-4020(02)00230-2

upstream raw materials:

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

methyl β-L-ribofuranoside

methyl 3-O-benzyl-β-L-ribofuranoside

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