4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside

Base Information

• Chemical Name: 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside
• CAS No.: 243120-93-6
• Molecular Formula: C₃₂H₄₇BrO₁₀
• Molecular Weight: 671.623
• Mol file: 243120-93-6.mol

Synonyms:4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside

Chemical Property of 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside

There total 4 articles about 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside 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: 100.0%

4-bromo-phenol (106-41-2) + 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl fluoride (187269-63-2) → 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside (243120-93-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0008-6215(99)00065-8

Reference yield:

penta-O-acetyl-D-mannose (66888-27-5) → 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside (243120-93-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / HF; pyridine / CH₂Cl₂ / 40 °C / sealed PFE flask

2: K₂CO₃ / methanol / 20 °C

3: 80 percent / 4-dimethylaminopyridine / pyridine / 0 - 70 °C

4: 100 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / 0 °C

With pyridine; dmap; boron trifluoride diethyl etherate; hydrogen fluoride; potassium carbonate; In pyridine; methanol; dichloromethane; 1: Fluorination / 2: Deacetylation / 3: Acylation / 4: Substitution;

DOI:10.1016/S0008-6215(99)00065-8

Reference yield:

α-D-mannopyranosyl fluoride (2713-54-4) → 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside (243120-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 4-dimethylaminopyridine / pyridine / 0 - 70 °C

2: 100 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / 0 °C

With dmap; boron trifluoride diethyl etherate; In pyridine; dichloromethane; 1: Acylation / 2: Substitution;

DOI:10.1016/S0008-6215(99)00065-8

upstream raw materials:

4-bromo-phenol

2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl fluoride

penta-O-acetyl-D-mannose

α-D-mannopyranosyl fluoride

Downstream raw materials:

4-bromophenyl α-D-mannopyranoside