3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide
• CAS No.: 73446-41-0
• Molecular Formula: C₂₀H₂₄BrNO₉
• Molecular Weight: 502.316

Synonyms:3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide

Chemical Property of 3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide

Chemical Property:

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Technology Process of 3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide

There total 3 articles about 3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl 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:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) → 3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide (73446-41-0)

Guidance literature:

With hydrogen bromide; In acetic acid; for 3h; Yield given; Ambient temperature;

DOI:10.1016/0008-6215(90)84077-8

Reference yield:

(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-((E)-(4-methoxybenzylidene)amino)tetrahydro-2Hpyran-2,4,5-triyl triacetate (7597-81-1,34948-61-3,55628-19-8,74554-00-0,103382-86-1,114297-26-6) → 3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide (73446-41-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 5.5 M HCl / acetone / Heating

2: 1. NaHCO₃ / 1. H₂O 2. CHCl₃, 1 h, room temperature

3: 33percent HBr / acetic acid / 3 h / Ambient temperature

With hydrogenchloride; hydrogen bromide; sodium hydrogencarbonate; In acetic acid; acetone;

DOI:10.1016/0008-6215(90)84077-8

Reference yield:

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) → 3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide (73446-41-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1. NaHCO₃ / 1. H₂O 2. CHCl₃, 1 h, room temperature

2: 33percent HBr / acetic acid / 3 h / Ambient temperature

With hydrogen bromide; sodium hydrogencarbonate; In acetic acid;

DOI:10.1016/0008-6215(90)84077-8

upstream raw materials:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-((E)-(4-methoxybenzylidene)amino)tetrahydro-2Hpyran-2,4,5-triyl triacetate

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

Downstream raw materials:

2,2,2-trichloroethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one

3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose

1-methylethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

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