Benzamide, N-(octahydro-1,7,8-trihydroxy-6-indolizinyl)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Base Information

• Chemical Name: Benzamide, N-(octahydro-1,7,8-trihydroxy-6-indolizinyl)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-
• CAS No.: 156205-96-8
• Molecular Formula: C₁₅H₂₀N₂O₄
• Molecular Weight: 292.335
• Mol file: 156205-96-8.mol

Synonyms:Benzamide, N-(octahydro-1,7,8-trihydroxy-6-indolizinyl)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Chemical Property of Benzamide, N-(octahydro-1,7,8-trihydroxy-6-indolizinyl)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzamide, N-(octahydro-1,7,8-trihydroxy-6-indolizinyl)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

There total 9 articles about Benzamide, N-(octahydro-1,7,8-trihydroxy-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:

6-O-benzoylcastanospermine (121104-76-5) → 6-amino-6-N-benzoyl-6-deoxycastanospermine (156205-96-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 74 percent / camphorsulfonic acid, triethylorthoformate / dimethylformamide / 1 h / 80 °C

2: diisopropylethylamine / toluene / 1 h / 90 °C

3: aq. NaOH / methanol / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

5: NaN₃ / dimethylsulfoxide / 2.5 h / 90 °C

6: H₂ / 10percent Pd/C / ethanol / 4 h

7: Et₃N / CH₂Cl₂ / 0.5 h

8: 30percent aq. trifluoroacetic acid / Ambient temperature

With sodium hydroxide; sodium azide; camphor-10-sulfonic acid; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

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

Reference yield:

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8) → 6-amino-6-N-benzoyl-6-deoxycastanospermine (156205-96-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) (Bu₃Sn)2O / 1.) toluene, reflux, 2 h; 2.) 0 deg C, overnight

2: 74 percent / camphorsulfonic acid, triethylorthoformate / dimethylformamide / 1 h / 80 °C

3: diisopropylethylamine / toluene / 1 h / 90 °C

4: aq. NaOH / methanol / Ambient temperature

5: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

6: NaN₃ / dimethylsulfoxide / 2.5 h / 90 °C

7: H₂ / 10percent Pd/C / ethanol / 4 h

8: Et₃N / CH₂Cl₂ / 0.5 h

9: 30percent aq. trifluoroacetic acid / Ambient temperature

With sodium hydroxide; sodium azide; camphor-10-sulfonic acid; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; trifluoroacetic acid; bis(tri-n-butyltin)oxide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

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

Reference yield:

1,8-O-cyclohexylidene-7-O-methoxymethylcastanospermine (156205-91-3) → 6-amino-6-N-benzoyl-6-deoxycastanospermine (156205-96-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

2: NaN₃ / dimethylsulfoxide / 2.5 h / 90 °C

3: H₂ / 10percent Pd/C / ethanol / 4 h

4: Et₃N / CH₂Cl₂ / 0.5 h

5: 30percent aq. trifluoroacetic acid / Ambient temperature

With sodium azide; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; dimethyl sulfoxide;

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

upstream raw materials:

6-O-benzoylcastanospermine

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

1,8-O-cyclohexylidene-7-O-methoxymethylcastanospermine

6-O-benzoyl-1,8-O-cyclohexylidenecastanospermine

Refernces