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

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 175979-05-2
• Molecular Formula: C₂₂H₂₉NO₁₀
• Molecular Weight: 467.473

Synonyms:Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester

There total 2 articles about Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester 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: 70.0%

4-Methoxybenzyl alcohol (105-13-5) + (3aS)-6c,7t-diacetoxy-5t-acetoxymethyl-2-methyl-(3ar,7ac)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole (20757-53-3) → Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester (175979-05-2)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 0.0833333h; Heating;

DOI:10.1016/0008-6215(95)00345-2

Reference yield:

1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3,76375-61-6) → Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester (175979-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / CF₃SO₃H / CH₂Cl₂ / 0.67 h / Ambient temperature

2: 70 percent / p-TsOH / benzene / 0.08 h / Heating

With trifluorormethanesulfonic acid; toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1016/0008-6215(95)00345-2

Reference yield: 95.0%

Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester (175979-05-2) → 4-methoxybenzyl-2-acetamido-2-deoxy-α-D-mannopyranose (175979-06-3)

Guidance literature:

With sodium methylate; In methanol; for 0.333333h;

DOI:10.1016/0008-6215(95)00345-2

upstream raw materials:

4-Methoxybenzyl alcohol

(3aS)-6c,7t-diacetoxy-5t-acetoxymethyl-2-methyl-(3ar,7ac)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole

1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose

Downstream raw materials:

4-methoxybenzyl-2-acetamido-2-deoxy-α-D-mannopyranose

Acetic acid (2S,3S,4R,5S,6R)-3-acetylamino-5-benzyloxy-6-hydroxymethyl-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester

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