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

Base Information

• Chemical Name: 1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside
• CAS No.: 824396-53-4
• Molecular Formula: C₃₆H₅₁NO₆
• Molecular Weight: 593.804

Synonyms:1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside

Chemical Property of 1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside

Chemical Property:

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Technology Process of 1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside

There total 3 articles about 1-dodecyl 2-acetamido-3-O-benzyl-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: 81.0%

benzyl bromide (100-39-0) + 1-dodecyl 2-acetamido-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-41-0) → 1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-53-4)

Guidance literature:

With potassium hydroxide; 18-crown-6 ether; In tetrahydrofuran; at 5 - 20 ℃;

DOI:10.1016/j.tetasy.2004.09.034

Reference yield:

(E)-cinnamaldehyde dimethylacetal (4364-06-1) → 1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / anhydrous camphorsulfonic acid / acetonitrile / 20 °C

2: 81 percent / potassium hydroxide; 18-crown-6 / tetrahydrofuran / 5 - 20 °C

With potassium hydroxide; 18-crown-6 ether; camphor-10-sulfonic acid; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tetasy.2004.09.034

Reference yield:

dodecyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside (147025-06-7) → 1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / anhydrous camphorsulfonic acid / acetonitrile / 20 °C

2: 81 percent / potassium hydroxide; 18-crown-6 / tetrahydrofuran / 5 - 20 °C

With potassium hydroxide; 18-crown-6 ether; camphor-10-sulfonic acid; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tetasy.2004.09.034

upstream raw materials:

benzyl bromide

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

(E)-cinnamaldehyde dimethylacetal

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

Downstream raw materials:

1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-[(2-phenylcyclopropyl)methylidene]-β-D-glucopyranoside

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