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

Base Information

• Chemical Name: 1-dodecyl 2-acetamido-3-O-benzyloxycarbonyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside
• CAS No.: 824396-63-6
• Molecular Formula: C₃₇H₅₁NO₈
• Molecular Weight: 637.814

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

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

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Technology Process of 1-dodecyl 2-acetamido-3-O-benzyloxycarbonyl-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-benzyloxycarbonyl-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: 73.0%

benzyl chloroformate (501-53-1,94274-21-2) + 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-benzyloxycarbonyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-63-6)

Guidance literature:

With pyridine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.tetasy.2004.09.034

Reference yield:

(E)-cinnamaldehyde dimethylacetal (4364-06-1) → 1-dodecyl 2-acetamido-3-O-benzyloxycarbonyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-63-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 73 percent / pyridine / tetrahydrofuran; CH₂Cl₂ / 48 h / 20 °C

With pyridine; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane; 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-benzyloxycarbonyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside (824396-63-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 73 percent / pyridine / tetrahydrofuran; CH₂Cl₂ / 48 h / 20 °C

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

DOI:10.1016/j.tetasy.2004.09.034

upstream raw materials:

benzyl chloroformate

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

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