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

Base Information

• Chemical Name: N¹-p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine
• CAS No.: 114656-12-1
• Molecular Formula: C₃₈H₅₆N₆O₁₃
• Molecular Weight: 804.895

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

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

Chemical Property:

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

There total 5 articles about N¹-p-(3,4,6-tri-O-acetyl-2-azido-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: 70.0%

N2,N3-di-tert-butoxycarbonylspermidine + p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamic acid (114643-37-7) → N1-p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N2,N3-di-tert-butoxycarbonylspermidine (114656-12-1)

Guidance literature:

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 22h; 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-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N2,N3-di-tert-butoxycarbonylspermidine (114656-12-1)

Guidance literature:

Multi-step reaction with 5 steps

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

2: Et₄NCl

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

4: 90 percent / 90percent CF₃CO₂H / 0.67 h / Ambient temperature

5: 70 percent / carbonyldiimidazole / tetrahydrofuran / 22 h / Ambient temperature

With tetraethylammonium chloride; hydrogen bromide; 1,1'-carbonyldiimidazole; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetic anhydride; acetic acid; N,N-dimethyl-formamide;

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

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride (67817-37-2) → N1-p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N2,N3-di-tert-butoxycarbonylspermidine (114656-12-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / dimethylformamide / 65 h / Ambient temperature

2: 90 percent / 90percent CF₃CO₂H / 0.67 h / Ambient temperature

3: 70 percent / carbonyldiimidazole / tetrahydrofuran / 22 h / Ambient temperature

With 1,1'-carbonyldiimidazole; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

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

upstream raw materials:

p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamic acid

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide

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