4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose

Base Information

• Chemical Name: 4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose
• CAS No.: 552849-02-2
• Molecular Formula: C₂₀H₂₅NO₆
• Molecular Weight: 375.422
• Mol file: 552849-02-2.mol

Synonyms:4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose

Chemical Property of 4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose

There total 4 articles about 4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose 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: 91.0%

acetic anhydride (108-24-7) + 3-N-allylamino-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose (552849-01-1) → 4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose (552849-02-2)

Guidance literature:

With dmap; triethylamine; In ethyl acetate; at 20 ℃; for 3h;

DOI:10.1021/jo034159g

Reference yield:

benzyl bromide (100-39-0) → 4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose (552849-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / tetrahydrofuran

2: 65 percent / dimethylformamide / 96 h / 120 °C

3: 91 percent / Et₃N; DMAP / ethyl acetate / 3 h / 20 °C

With dmap; sodium hydride; triethylamine; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo034159g

Reference yield:

1,6:3,4-dianhydro-2-O-benzyl-β-D-altropyranose (213594-43-5) → 4-O-acetyl-3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose (552849-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / dimethylformamide / 96 h / 120 °C

2: 91 percent / Et₃N; DMAP / ethyl acetate / 3 h / 20 °C

With dmap; triethylamine; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo034159g

upstream raw materials:

acetic anhydride

3-N-allylamino-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose

benzyl bromide

1,6:3,4-dianhydro-2-O-benzyl-β-D-altropyranose

Downstream raw materials:

3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-deoxy-β-D-mannopyranose

3-(N-acetyl-N-allylamino)-1,6-anhydro-2-O-benzyl-3-keto-β-D-lyxo-hexopyranose