Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-yl ester
• CAS No.: 474426-79-4
• Molecular Formula: C₂₀H₂₃NO₁₀
• Molecular Weight: 437.403

Synonyms:Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-yl ester

There total 2 articles about Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-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%

aniline (62-53-3) + acetic 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic anhydride (474426-72-7) → Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-yl ester (474426-79-4)

Guidance literature:

In dichloromethane; for 25h;

DOI:10.1021/ol026629j

Reference yield:

aniline (62-53-3) + 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid (62133-77-1,67919-37-3,83023-73-8,85165-61-3,95722-13-7,98301-58-7,103730-05-8,104195-04-2) → Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-yl ester (474426-79-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo0501994

Reference yield: 90.0%

Acetic acid (2S,3S,4S,5R,6S)-4,5,6-triacetoxy-2-phenylcarbamoyl-tetrahydro-pyran-3-yl ester (474426-79-4) → 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranosiduronic acid N-phenylamide (926641-71-6)

Guidance literature:

With hydrogen bromide; In acetic acid;

DOI:10.1016/j.carres.2006.10.023

upstream raw materials:

aniline

acetic 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic anhydride

1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid

Downstream raw materials:

2,3,4-tri-O-acetyl-1-chloro-1-deoxy-α-D-glucopyranuron-N-phenylamide

2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranosiduronic acid N-phenylamide

2,3,4-tri-O-acetyl-1,6-anhydro-6-Z-phenylimino-β-D-glucopyranose

phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranuric acid N-phenylamide

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