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

Base Information

• Chemical Name: Acetamide, N-(octahydro-1,7,8-trihydroxy-6-indolizinyl)-N-(phenylmethyl)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-
• CAS No.: 156206-16-5
• Molecular Formula: C₁₇H₂₄N₂O₄
• Molecular Weight: 320.389
• Mol file: 156206-16-5.mol

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

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

There total 9 articles about Acetamide, N-(octahydro-1,7,8-trihydroxy-6-indolizinyl)-N-(phenylmethyl)-, 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-N-benzylacetamino-6-deoxycastanospermine (156206-16-5)

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: 47 percent / dimethylsulfoxide / 24 h / 90 °C

6: 93 percent / 30percent aq. trifluoroacetic acid / 18 h / Ambient temperature

7: pyridine / Ambient temperature

8: NaOMe / methanol / Ambient temperature

With pyridine; sodium hydroxide; camphor-10-sulfonic acid; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; trifluoroacetic acid; In methanol; 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-N-benzylacetamino-6-deoxycastanospermine (156206-16-5)

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: 47 percent / dimethylsulfoxide / 24 h / 90 °C

7: 93 percent / 30percent aq. trifluoroacetic acid / 18 h / Ambient temperature

8: pyridine / Ambient temperature

9: NaOMe / methanol / Ambient temperature

With pyridine; sodium hydroxide; camphor-10-sulfonic acid; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; trifluoroacetic acid; bis(tri-n-butyltin)oxide; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

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

Reference yield:

6-amino-6-N-benzyl-6-deoxycastanospermine (156205-85-5) → 6-N-benzylacetamino-6-deoxycastanospermine (156206-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / Ambient temperature

2: NaOMe / methanol / Ambient temperature

With pyridine; sodium methylate; In methanol;

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

6-amino-6-N-benzyl-6-deoxycastanospermine

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

Refernces