Acetamide, N-1,7,8-tris(acetyloxy)octahydro-6-indolizinyl-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Base Information

• Chemical Name: Acetamide, N-1,7,8-tris(acetyloxy)octahydro-6-indolizinyl-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-
• CAS No.: 156205-53-7
• Molecular Formula: C₁₆H₂₄N₂O₇
• Molecular Weight: 356.376
• Mol file: 156205-53-7.mol

Synonyms:Acetamide, N-1,7,8-tris(acetyloxy)octahydro-6-indolizinyl-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Chemical Property of Acetamide, N-1,7,8-tris(acetyloxy)octahydro-6-indolizinyl-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Chemical Property:

• PSA: 111.24000
• LogP: -0.29710

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Acetamide, N-1,7,8-tris(acetyloxy)octahydro-6-indolizinyl-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

There total 9 articles about Acetamide, N-1,7,8-tris(acetyloxy)octahydro-6-indolizinyl-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)- 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:

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8) → 6-acetamido-1,7,8-tri-O-acetyl-6-deoxycastanospermine (156205-53-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / pyridine / 0 deg C -> r.t., overnight

2: 30 percent / tributyltin methoxide / tetrahydrofuran / Heating

3: 86 percent / pyridine

4: 56 percent / NaN₃ / dimethylsulfoxide / 80 deg C, 1 h; 60 deg C, overnight

5: 81 percent / H₂ / 5percent Pd/C / toluene / 24 h

6: 101 percent / pyridine / Ambient temperature

With pyridine; sodium azide; hydrogen; tributyltin methoxide; palladium on activated charcoal; In tetrahydrofuran; pyridine; dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4020(01)85075-4

Reference yield:

1,6,7,8-tetra-O-acetylcastanospermine (79831-77-9,185907-14-6) → 6-acetamido-1,7,8-tri-O-acetyl-6-deoxycastanospermine (156205-53-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 30 percent / tributyltin methoxide / tetrahydrofuran / Heating

2: 86 percent / pyridine

3: 56 percent / NaN₃ / dimethylsulfoxide / 80 deg C, 1 h; 60 deg C, overnight

4: 81 percent / H₂ / 5percent Pd/C / toluene / 24 h

5: 101 percent / pyridine / Ambient temperature

With pyridine; sodium azide; hydrogen; tributyltin methoxide; palladium on activated charcoal; In tetrahydrofuran; pyridine; dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4020(01)85075-4

Reference yield:

6-O-carboxybenzylcastenospermine (156205-43-5) → 6-acetamido-1,7,8-tri-O-acetyl-6-deoxycastanospermine (156205-53-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / pyridine / Ambient temperature

2: 73 percent / H₂ / 5percent Pd/C / ethyl acetate; ethanol / 3102.9 Torr

3: 86 percent / pyridine

4: 56 percent / NaN₃ / dimethylsulfoxide / 80 deg C, 1 h; 60 deg C, overnight

5: 81 percent / H₂ / 5percent Pd/C / toluene / 24 h

6: 101 percent / pyridine / Ambient temperature

With pyridine; sodium azide; hydrogen; palladium on activated charcoal; In pyridine; ethanol; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1016/S0040-4020(01)85075-4

upstream raw materials:

acetic anhydride

1,7,8-tri-O-acetyl-6-amino-6-deoxycastanospermine

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine

1,6,7,8-tetra-O-acetylcastanospermine

Downstream raw materials:

6-acetamido-6-deoxycastanospermine