2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose

Base Information

• Chemical Name: 2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose
• CAS No.: 142269-90-7
• Molecular Formula: C₁₇H₂₁NO₆
• Molecular Weight: 335.357

Synonyms:2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose

Chemical Property of 2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose

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Technology Process of 2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose

There total 3 articles about 2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose 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: 75.0%

2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-6-O-(2,4,6-trimethylphenylsulfonyl)-D-glucopyranose → 2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose (142269-90-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; for 10h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90550-0

Reference yield: 70.0%

2-allyloxycarbonylamino-1,6-anhydro-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose (142269-89-4) → 2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose (142269-90-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃; for 15h;

DOI:10.1016/S0008-6215(00)90550-0

Reference yield:

2-N-Allyloxycarbonyl-2-amino-1,6-anhydro-2-deoxy-β-D-glucopyranose (121363-69-7) → 2-Allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-desoxy-β-D-glucopyranose (142269-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaH / tetrahydrofuran / 15 h / Ambient temperature

2: 70 percent / TiCl₄ / CH₂Cl₂ / 15 h / 0 °C

With titanium tetrachloride; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0008-6215(00)90550-0

upstream raw materials:

2-allyloxycarbonylamino-1,6-anhydro-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose

2-N-Allyloxycarbonyl-2-amino-1,6-anhydro-2-deoxy-β-D-glucopyranose

Downstream raw materials:

2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose

4-O-(3,4,6-Tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-2-allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose

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