N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine

Base Information

• Chemical Name: N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine
• CAS No.: 300362-77-0
• Molecular Formula: C₃₀H₃₅NO₁₃
• Molecular Weight: 617.607
• Mol file: 300362-77-0.mol

Synonyms:N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine

Chemical Property of N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine

There total 1 articles about N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine 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: 18.0%

N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine (37034-22-3) + β-D-glucose pentaacetate (604-69-3) → N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine (300362-77-0) + N-benzyloxycarbonyl-3,4-dihydroxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine (300362-76-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 4h;

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

Reference yield: 97.0%

N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine (300362-77-0) → {2-[3-Hydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-ethyl}-carbamic acid benzyl ester

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1.5h;

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

Reference yield:

N-benzyloxycarbonyl-3,4-dihydroxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylethylamine (300362-77-0) → 3,4-dihydroxy-4-O-(β-D-glucopyranosyl)phenylethylammonium trifluoroacetate

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NaOMe / methanol / 1.5 h / 20 °C

2: 99 percent / TFA; H₂ / Pd-C / methanol / 1 h / 20 °C

With hydrogen; sodium methylate; trifluoroacetic acid; palladium on activated charcoal; In methanol; 1: Elimination / 2: Hydrogenolysis;

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

upstream raw materials:

N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine

β-D-glucose pentaacetate