N¹-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine

Base Information

• Chemical Name: N¹-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine
• CAS No.: 114643-42-4
• Molecular Formula: C₄₀H₆₀N₄O₁₄
• Molecular Weight: 820.935

Synonyms:N¹-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine

Chemical Property of N¹-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine

Chemical Property:

Purity/Quality:

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Technology Process of N¹-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine

There total 11 articles about N¹-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine 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: 77.0%

N2,N3-di-tert-butoxycarbonylspermidine + p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)cinnamic acid (114656-11-0) → N1-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyloxy)cinnamoyl-N2,N3-di-tert-butoxycarbonylspermidine (114643-42-4,114643-43-5)

Guidance literature:

With dmap; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; for 120h; Ambient temperature;

DOI:10.1016/0008-6215(87)80249-5

Reference yield: 65.0%

N2,N3-di-tert-butoxycarbonylspermidine + p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamic acid (114643-39-9) → N1-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N2,N3-di-tert-butoxycarbonylspermidine (114643-42-4)

Guidance literature:

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1016/0008-6215(87)80249-5

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose (67817-30-5) → N1-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N2,N3-di-tert-butoxycarbonylspermidine (114643-42-4)

Guidance literature:

Multi-step reaction with 7 steps

1: HBr / CH₂Cl₂; acetic anhydride; acetic acid / 1 h / 0 °C

2: Et₄NCl

3: 55 percent / dimethylformamide / 65 h / Ambient temperature

4: quinoline, H₂ / 5percent Pd-BaSO₄ / methanol

5: pyridine

6: 78 percent / 90percent CF₃CO₂H / 1 h / Ambient temperature

7: 65 percent / carbonyldiimidazole / tetrahydrofuran / 20 h / Ambient temperature

With pyridine; quinoline; tetraethylammonium chloride; hydrogen bromide; hydrogen; 1,1'-carbonyldiimidazole; trifluoroacetic acid; palladium on barium sulfate; In tetrahydrofuran; methanol; dichloromethane; acetic anhydride; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(87)80249-5

upstream raw materials:

p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)cinnamic acid

4-hydroxy-trans-cinnamic acid tert-butyl ester

Sodium; 4-((E)-2-tert-butoxycarbonyl-vinyl)-phenolate

tert-butyl p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)cinnamate

Downstream raw materials:

N¹-cinnamoylspermidine dihydrochloride

N¹-cinnamoylspermidine dihydrochloride

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