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

Base Information

• Chemical Name: p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamic acid
• CAS No.: 114643-40-2
• Molecular Formula: C₂₀H₂₆N₄O₇
• Molecular Weight: 434.449
• Mol file: 114643-40-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamic acid 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: 96.0%

ethyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate (83022-03-1) → p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamic acid (114643-40-2)

Guidance literature:

With potassium hydroxide; In methanol; for 12h; Ambient temperature;

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

Reference yield:

tert-butyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-6-O-tolylsulfonyl-α-D-glucopyranosyloxy>cinnamate (114643-52-6) → p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamic acid (114643-40-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaCNBH₃, NaI / hexamethylphosphoric acid triamide / 20 h / 70 - 80 °C

2: 1) 90percent CF₃CO₂H, 2) di-tert-butyl dicarbonate / 1) 1.5 h, RT, 2) 4 h, RT

With di-tert-butyl dicarbonate; sodium cyanoborohydride; trifluoroacetic acid; sodium iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

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

Reference yield:

tert-butyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate (114643-41-3) → p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamic acid (114643-40-2)

Guidance literature:

With di-tert-butyl dicarbonate; trifluoroacetic acid; Yield given. Multistep reaction; 1) 1.5 h, RT, 2) 4 h, RT;

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

upstream raw materials:

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

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

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