Indolizine, 8-fluorooctahydro-1,2,7-tris(phenylmethoxy)-, 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-

Base Information

• Chemical Name: Indolizine, 8-fluorooctahydro-1,2,7-tris(phenylmethoxy)-, 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-
• CAS No.: 156150-91-3
• Molecular Formula: C₂₉H₃₂FNO₃
• Molecular Weight: 461.576
• Mol file: 156150-91-3.mol

Synonyms:Indolizine, 8-fluorooctahydro-1,2,7-tris(phenylmethoxy)-, 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-

Chemical Property of Indolizine, 8-fluorooctahydro-1,2,7-tris(phenylmethoxy)-, 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-

Chemical Property:

• PSA: 30.93000
• LogP: 5.10650

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Indolizine, 8-fluorooctahydro-1,2,7-tris(phenylmethoxy)-, 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-

There total 3 articles about Indolizine, 8-fluorooctahydro-1,2,7-tris(phenylmethoxy)-, 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)- 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) → 1,2,7-tri-O-benzyl-8-fluoro-1(R),2(S),7(S),8(R),8a(R)-trihydroxyoctahydroindolizidine (156150-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.)Bu₂SnO, 2.) Bu₄NBr, 3.) LiH, Pr-SH / 1.) MePh, reflux, 2 h, 2.) MePh, reflux, 3 days, 3.) DMSO, 3 h

2: DAST / CH₂Cl₂ / 48 h

With 1-thiopropane; tetrabutylammomium bromide; lithium hydride; di(n-butyl)tin oxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane;

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

Reference yield:

1,6,7-tri-O-benzylcastanospermine (156150-89-9) → 1,2,7-tri-O-benzyl-8-fluoro-1(R),2(S),7(S),8(R),8a(R)-trihydroxyoctahydroindolizidine (156150-91-3) + 1,6,7-tri-O-benzyl-8-deoxy-8-fluorocastanospermine (156150-90-2)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; Yield given. Yields of byproduct given;

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

Reference yield:

benzyl bromide (100-39-0) → 1,2,7-tri-O-benzyl-8-fluoro-1(R),2(S),7(S),8(R),8a(R)-trihydroxyoctahydroindolizidine (156150-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.)Bu₂SnO, 2.) Bu₄NBr, 3.) LiH, Pr-SH / 1.) MePh, reflux, 2 h, 2.) MePh, reflux, 3 days, 3.) DMSO, 3 h

2: DAST / CH₂Cl₂ / 48 h

With 1-thiopropane; tetrabutylammomium bromide; lithium hydride; di(n-butyl)tin oxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane;

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

upstream raw materials:

1,6,7-tri-O-benzylcastanospermine

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

benzyl bromide

Downstream raw materials:

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