cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside

Base Information

• Chemical Name: cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside
• CAS No.: 824396-60-3
• Molecular Formula: C₂₅H₃₃NO₇
• Molecular Weight: 459.54

Synonyms:cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside

Chemical Property of cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside

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Technology Process of cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside

There total 3 articles about cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 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: 63.0%

acetic anhydride (108-24-7) + cyclohexyl 2-acetamido-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-38-5) → cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-60-3)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetasy.2004.09.034

Reference yield:

cyclohexyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside (21559-72-8) → cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / anhydrous camphorsulfonic acid / acetonitrile / 20 °C

2: 63 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; camphor-10-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.tetasy.2004.09.034

Reference yield:

(E)-cinnamaldehyde dimethylacetal (4364-06-1) → cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / anhydrous camphorsulfonic acid / acetonitrile / 20 °C

2: 63 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; camphor-10-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.tetasy.2004.09.034

upstream raw materials:

acetic anhydride

cyclohexyl 2-acetamido-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside

cyclohexyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside

(E)-cinnamaldehyde dimethylacetal

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