N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Base Information

• Chemical Name: N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate
• CAS No.: 247075-43-0
• Molecular Formula: C₂₁H₂₄BrNO₁₂
• Molecular Weight: 562.325
• Mol file: 247075-43-0.mol

Synonyms:N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Chemical Property of N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

There total 7 articles about N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 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: 94.0%

N-(4-carboxy-3-bromophenyl) O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate (247075-42-9) → N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate (247075-43-0)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0968-0896(99)00095-4

Reference yield:

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) → N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate (247075-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 294 mg / Et₃N / toluene / 20 °C

2: 100 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h / 20 °C

3: 94 percent / BH₃-THF / tetrahydrofuran / 20 °C

With morpholine; borane-THF; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; toluene; 1: Addition / 2: deallylation / 3: Reduction;

DOI:10.1016/S0968-0896(99)00095-4

Reference yield:

2-bromo-1,4-benzenedicarboxylic acid (586-35-6) → N-[4-(hydroxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate (247075-43-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 26 percent / DMAP; DCC / tetrahydrofuran / 0 - 20 °C

2: diphenylphosphoryl azide; Et₃N / toluene / 20 °C

3: toluene / 1 h / 85 °C

4: 294 mg / Et₃N / toluene / 20 °C

5: 100 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h / 20 °C

6: 94 percent / BH₃-THF / tetrahydrofuran / 20 °C

With morpholine; dmap; borane-THF; diphenylphosphoranyl azide; triethylamine; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; toluene; 1: Esterification / 2: Substitution / 3: Curtius rearrangement / 4: Addition / 5: deallylation / 6: Reduction;

DOI:10.1016/S0968-0896(99)00095-4

upstream raw materials:

N-(4-carboxy-3-bromophenyl) O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

2-bromo-1,4-benzenedicarboxylic acid

3-bromoterephthalic acid 4-O-allyl ester