ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate

Base Information

• Chemical Name: ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate
• CAS No.: 83022-03-1
• Molecular Formula: C₂₂H₃₀N₄O₇
• Molecular Weight: 462.503

Synonyms:ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate

Chemical Property of ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate

Chemical Property:

Purity/Quality:

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Technology Process of ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate

There total 21 articles about ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate 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: 79.0%

ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-6-O-p-tolylsulfonyl-α-D-glucopyranosyloxy>cinnamate (83022-02-0) → ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate (83022-03-1)

Guidance literature:

With sodium cyanoborohydride; sodium iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 70 - 75 ℃; for 15h;

DOI:10.1016/S0040-4039(00)87195-6

Reference yield:

ethyl (E)-4-hydroxycinnamate (2979-06-8,7361-92-4,7362-39-2) → ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate (83022-03-1)

Guidance literature:

Multi-step reaction with 9 steps

1: AgClO₄, Ag₂CO₃, molecular sieve / CH₂Cl₂ / 24 h / Ambient temperature

2: Na/EtOH / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 90 percent / H₂, quinoline / 5percent Pd-BaSO₄ / methanol / 20 h / 760 Torr / Ambient temperature

4: 87 percent / Et₃N / dioxane; H₂O / 16 h

5: pyridine

6: 60 percent / NaN₃ / hexamethylphosphoric acid triamide / 15 h / 80 °C

7: 95 percent / Na/EtOH / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 96 percent / pyridine

9: 74 percent / NaI, NaBH₃CN / hexamethylphosphoric acid triamide / 16 h / 70 - 75 °C

With quinoline; sodium azide; molecular sieve; ethanol; hydrogen; silver perchlorate; sodium; sodium cyanoborohydride; triethylamine; silver carbonate; sodium iodide; palladium on barium sulfate; In 1,4-dioxane; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;

DOI:10.1016/0008-6215(82)84035-4

Reference yield:

ethyl p-hydroxycinnamate trimethylsilyl ether (83021-95-8) → ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate (83022-03-1)

Guidance literature:

Multi-step reaction with 9 steps

1: AgClO₄, Ag₂CO₃, molecular sieve / CH₂Cl₂ / 24 h / Ambient temperature

2: Na/EtOH / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 90 percent / H₂, quinoline / 5percent Pd-BaSO₄ / methanol / 20 h / 760 Torr / Ambient temperature

4: 87 percent / Et₃N / dioxane; H₂O / 16 h

5: pyridine

6: 60 percent / NaN₃ / hexamethylphosphoric acid triamide / 15 h / 80 °C

7: 95 percent / Na/EtOH / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 96 percent / pyridine

9: 74 percent / NaI, NaBH₃CN / hexamethylphosphoric acid triamide / 16 h / 70 - 75 °C

With quinoline; sodium azide; molecular sieve; ethanol; hydrogen; silver perchlorate; sodium; sodium cyanoborohydride; triethylamine; silver carbonate; sodium iodide; palladium on barium sulfate; In 1,4-dioxane; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;

DOI:10.1016/0008-6215(82)84035-4

upstream raw materials:

ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-6-O-p-tolylsulfonyl-α-D-glucopyranosyloxy>cinnamate

ethyl (E)-4-hydroxycinnamate

ethyl p-hydroxycinnamate trimethylsilyl ether

ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-α-D-glucopyranosyloxy>cinnamate

Downstream raw materials:

ethyl p-<4-amino-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate

p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamic acid

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