Carbonic acid, octahydro-1,7,8-trihydroxy-6-indolizinyl phenylmethyl ester, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Base Information

• Chemical Name: Carbonic acid, octahydro-1,7,8-trihydroxy-6-indolizinyl phenylmethyl ester, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-
• CAS No.: 156205-43-5
• Molecular Formula: C₁₆H₂₁NO₆
• Molecular Weight: 323.346
• Mol file: 156205-43-5.mol

Synonyms:Carbonic acid, octahydro-1,7,8-trihydroxy-6-indolizinyl phenylmethyl ester, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

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

Chemical Property:

• PSA: 99.46000
• LogP: -0.18310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbonic acid, octahydro-1,7,8-trihydroxy-6-indolizinyl phenylmethyl ester, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

There total 1 articles about Carbonic acid, octahydro-1,7,8-trihydroxy-6-indolizinyl phenylmethyl ester, 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) + benzyl chloroformate (501-53-1,94274-21-2) → 6-O-carboxybenzylcastenospermine (156205-43-5)

Guidance literature:

With bis(tri-n-butyltin)oxide; Yield given. Multistep reaction; 1.) toluene, reflux, 3 h; 2.) r.t., 2 h;

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

Reference yield: 76.0%

acetic anhydride (108-24-7) + 6-O-carboxybenzylcastenospermine (156205-43-5) → 1,7,8-tri-O-acetyl-6-O-carboxybenzylcastenospermine (156205-44-6)

Guidance literature:

With pyridine; Ambient temperature;

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

Reference yield:

6-O-carboxybenzylcastenospermine (156205-43-5) → 8-O-benzylcastanospermine (156205-70-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / pyridine / Ambient temperature

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

3: 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 1 h

4: 20 percent / 1 h / Heating

5: 82 percent / NaOMe / methanol

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; hydrogen; sodium methylate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; ethyl acetate;

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

upstream raw materials:

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

benzyl chloroformate

Downstream raw materials:

1,7,8-tri-O-acetyl-6-O-carboxybenzylcastenospermine

(+)-6-deoxy-6-fluorocastanospermine

6,7-Diepicastanospermine

6-amino-6-deoxycastanospermine