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

Base Information

• Chemical Name: tert-butyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-6-O-tolylsulfonyl-α-D-glucopyranosyloxy>cinnamate
• CAS No.: 114643-52-6
• Molecular Formula: C₃₁H₄₀N₄O₁₀S
• Molecular Weight: 660.745
• Mol file: 114643-52-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about tert-butyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-6-O-tolylsulfonyl-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:

(E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester (114643-51-5) + benzenesulfonyl chloride (98-09-9) → tert-butyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-6-O-tolylsulfonyl-α-D-glucopyranosyloxy>cinnamate (114643-52-6)

Guidance literature:

With pyridine; for 20h; Yield given; Ambient temperature;

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

Reference yield: 80.0%

tert-butyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4-dideoxy-6-O-tolylsulfonyl-α-D-glucopyranosyloxy>cinnamate (114643-52-6) → tert-butyl p-<4-azido-2-(tert-butoxycarbonyl)amino-2,4,6-trideoxy-α-D-glucopyranosyloxy>cinnamate (114643-41-3)

Guidance literature:

With sodium cyanoborohydride; sodium iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 70 - 80 ℃; for 20h;

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

upstream raw materials:

(E)-3-[4-((2R,3R,4R,5S,6S)-5-Azido-3-tert-butoxycarbonylamino-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester

benzenesulfonyl chloride

Downstream raw materials:

tert-butyl p-<4-azido-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