benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside
• CAS No.: 300362-72-5
• Molecular Formula: C₃₉H₄₃NO₁₀
• Molecular Weight: 685.771
• Mol file: 300362-72-5.mol

Synonyms:benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside

Chemical Property of benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside

There total 9 articles about benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside 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:

N-[2-(3,4-Bis-benzyloxy-phenyl)-ethyl]-succinamic acid (2R,3R,4S,5R,6R)-6-benzyloxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester (446302-69-8) → benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside (300362-72-5)

Guidance literature:

With trifluoroacetic acid; In nitromethane; at 0 ℃; for 1h;

DOI:10.1016/S0008-6215(00)00073-2

Reference yield:

benzyl 2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside (18978-00-2) → benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside (300362-72-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / acetone; methanol; acetic acid / 2 h / 0 °C

2: DMAP; DCC / CH₂Cl₂ / 3 h / 20 °C

3: 76 mg / TFA / nitromethane / 1 h / 0 °C

With dmap; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; nitromethane; dichloromethane; acetic acid; acetone; 1: Elimination / 2: Condensation / 3: Elimination;

DOI:10.1016/S0008-6215(00)00073-2

Reference yield:

N-(tert-butoxycarbonyl)dopamine (37034-31-4) → benzyl 6-O-[N-(3,4-dibenzyloxyphenylethyl)succinamyl]-β-D-glucopyranoside (300362-72-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

2: 95 percent / CF₃COOH / CH₂Cl₂ / 5 h / 20 °C

3: 94 percent / pyridine / 3 h / 20 °C

4: DMAP; DCC / CH₂Cl₂ / 3 h / 20 °C

5: 76 mg / TFA / nitromethane / 1 h / 0 °C

With dmap; potassium carbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; nitromethane; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Elimination / 3: Acylation / 4: Condensation / 5: Elimination;

DOI:10.1016/S0008-6215(00)00073-2

upstream raw materials:

N-[2-(3,4-Bis-benzyloxy-phenyl)-ethyl]-succinamic acid (2R,3R,4S,5R,6R)-6-benzyloxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

benzyl 2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside

N-(tert-butoxycarbonyl)dopamine

dopamine hydrochloride