3,4,6-tri-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranosyl bromide

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranosyl bromide
• CAS No.: 74564-13-9
• Molecular Formula: C₂₀H₂₄BrNO₈
• Molecular Weight: 486.316

Synonyms:3,4,6-tri-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranosyl bromide

Chemical Property of 3,4,6-tri-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranosyl bromide

Chemical Property:

Purity/Quality:

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Technology Process of 3,4,6-tri-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranosyl bromide

There total 2 articles about 3,4,6-tri-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranosyl bromide 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: 90.0%

1,3,4,6-tetra-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranose (74554-00-0) → 3,4,6-tri-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranosyl bromide (74564-13-9)

Guidance literature:

With hydrogen bromide; In chloroform; acetic acid; at 20 ℃; for 2.5h;

DOI:10.1007/BF00961768

Reference yield:

2-(4'-methoxybenzylidene)amino-2-desoxy-D-galactose (51471-40-0) → 3,4,6-tri-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranosyl bromide (74564-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridine / 24 h / 20 °C

2: 90 percent / HBr / CHCl₃; acetic acid / 2.5 h / 20 °C

With hydrogen bromide; In pyridine; chloroform; acetic acid;

DOI:10.1007/BF00961768

Reference yield: 33.0%

dibenzyl tributylstannyl phosphate (79940-50-4) + 3,4,6-tri-O-acetyl-2-deoxy-2-(p-methoxybenzylideneamino)-α-D-glucopyranosyl bromide (51884-88-9,61567-93-9,74564-13-9) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-amino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yl ester (79940-52-6) + Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphoryloxy)-5-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-tetrahydro-pyran-4-yl ester (79940-51-5)

Guidance literature:

With tetraethylammonium bromide; In 1,2-dichloro-ethane; at 40 ℃; for 3h;

DOI:10.1016/S0008-6215(00)85307-0

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranose

2-(4'-methoxybenzylidene)amino-2-desoxy-D-galactose

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-amino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphoryloxy)-5-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-tetrahydro-pyran-4-yl ester

3,4,6-tri-O-acetyl-2-<(hexadecanoyl)amino>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate

3,4,6-tri-O-acetyl-2-<(tetradecanoyl)amino>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate

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