1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose

Base Information

• Chemical Name: 1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose
• CAS No.: 173207-78-8
• Molecular Formula: C₄₆H₄₃BrO₁₇
• Molecular Weight: 947.741

Synonyms:1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose

Chemical Property of 1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose

Chemical Property:

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Technology Process of 1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose

There total 5 articles about 1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose 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: 92.0%

(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->2)-1,3,4,6-tetra-O-acetyl-β-D-mannopyranose (158717-30-7) → 1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose (173207-78-8)

Guidance literature:

With 3 A molecular sieve; hydrogen bromide; In dichloromethane; acetic acid; for 1h; Ambient temperature;

Reference yield:

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide (14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4) → 1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose (173207-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: AgOTf; 2,6-di-tert-butyl-4-methylpyridine / -55 - -40 °C

2: HBr; AcOH / CH₂Cl₂ / 4 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; hydrogen bromide; silver trifluoromethanesulfonate; acetic acid; In dichloromethane;

DOI:10.1039/b202022j

Reference yield:

1,3,4,6-tetra-O-acetyl-β-D-mannopyranose (18968-05-3) → 1-bromo-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranose (173207-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: AgOTf; 2,6-di-tert-butyl-4-methylpyridine / -55 - -40 °C

2: HBr; AcOH / CH₂Cl₂ / 4 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; hydrogen bromide; silver trifluoromethanesulfonate; acetic acid; In dichloromethane;

DOI:10.1039/b202022j

upstream raw materials:

(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->2)-1,3,4,6-tetra-O-acetyl-β-D-mannopyranose

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

1,3,4,6-tetra-O-acetyl-β-D-mannopyranose

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside

Downstream raw materials:

C₆₀H₆₂O₂₇

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