8-Indolizinol, octahydro-1,6,7-tris(phenylmethoxy)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Base Information

• Chemical Name: 8-Indolizinol, octahydro-1,6,7-tris(phenylmethoxy)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-
• CAS No.: 156150-89-9
• Molecular Formula: C₂₉H₃₃NO₄
• Molecular Weight: 459.585
• Mol file: 156150-89-9.mol

Synonyms:8-Indolizinol, octahydro-1,6,7-tris(phenylmethoxy)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Chemical Property of 8-Indolizinol, octahydro-1,6,7-tris(phenylmethoxy)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

Chemical Property:

• Boiling Point: 593.4±50.0 °C(Predicted)
• PKA: 13.44±0.70(Predicted)
• PSA: 51.16000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 4.12930

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 8-Indolizinol, octahydro-1,6,7-tris(phenylmethoxy)-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-

There total 2 articles about 8-Indolizinol, octahydro-1,6,7-tris(phenylmethoxy)-, 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 bromide (100-39-0) → (1S,6S,7R,8R,8aR)-1,6,8-Tris-benzyloxy-octahydro-indolizin-7-ol + 1,6,7-tri-O-benzylcastanospermine (156150-89-9)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; lithium n-propylmercaptide; Multistep reaction. Title compound not separated from byproducts; 1.) toluene, ref., 3 day; 2.) DMSO;

DOI:10.1016/S0040-4039(00)76852-3

Reference yield:

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8) + benzyl bromide (100-39-0) → 1,6,7-tri-O-benzylcastanospermine (156150-89-9) + 1,2,7-tri-O-benzyl-1(R),2(S),7(S),8(R),8a(R)-tetrahydroxyoctahydroindolizidine (171925-19-2)

Guidance literature:

With 1-thiopropane; tetrabutylammomium bromide; lithium hydride; di(n-butyl)tin oxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) MePh, reflux, 2 h, 2.) MePh, reflux, 3 days, 3.) DMSO, 3 h;

DOI:10.1016/0040-4020(95)00803-G

Reference yield: 63.0%

pivaloyl chloride (3282-30-2) + 1,6,7-tri-O-benzylcastanospermine (156150-89-9) → 1,6,7-tri-O-benzyl-8-O-pivaloylcastanospermine (171925-40-9)

Guidance literature:

With pyridine; at 70 ℃; for 30h;

DOI:10.1016/0040-4020(95)00803-G

upstream raw materials:

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

benzyl bromide

Downstream raw materials:

1,2,7-tri-O-benzyl-8-fluoro-1(R),2(S),7(S),8(R),8a(R)-trihydroxyoctahydroindolizidine

1,6,7-tri-O-benzyl-8-deoxy-8-fluorocastanospermine

1,6,7-tri-O-benzyl-8-O-pivaloylcastanospermine

8-deoxy-8-fluorocastanospermine