2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-diphenylcarbamoylguanine

Base Information

• Chemical Name: 2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-diphenylcarbamoylguanine
• CAS No.: 648916-77-2
• Molecular Formula: C₄₀H₃₅N₇O₁₂
• Molecular Weight: 805.758
• Mol file: 648916-77-2.mol

Synonyms:2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-diphenylcarbamoylguanine

Chemical Property of 2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-diphenylcarbamoylguanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-diphenylcarbamoylguanine

There total 2 articles about 2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-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: 54.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate (87190-67-8) + N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) → 2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-diphenylcarbamoylguanine (648916-77-2)

Guidance literature:

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine; With benzenesulfonamide; In 1,2-dichloro-ethane; at 80 ℃; for 0.5h;

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate; With trimethylsilyl trifluoromethanesulfonate; In toluene; at 80 ℃; for 0.75h;

DOI:10.1016/j.tetlet.2003.10.070

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3) → 2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-diphenylcarbamoylguanine (648916-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DBU

2.1: BSA / 1,2-dichloro-ethane / 0.5 h / 80 °C

2.2: 54 percent / trimethylsilyl trifluoromethylsulfonate / toluene / 0.75 h / 80 °C

With benzenesulfonamide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-ethane; 2.2: Vorbrueggen coupling;

DOI:10.1016/j.tetlet.2003.10.070

Reference yield: 31.0%

2-N-acetyl-9-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-diphenylcarbamoylguanine (648916-77-2) → 9-[2-N-(2-carboxamidobenzoyl)amino-2-deoxy-β-D-glucopyranosyl]guanine

Guidance literature:

With ammonia; In methanol; at -12 - 20 ℃; for 64h;

DOI:10.1016/j.tetlet.2003.10.070

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose