1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-

Base Information

• Chemical Name: 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-
• CAS No.: 171925-21-6
• Molecular Formula: C₁₆H₂₃NO₈
• Molecular Weight: 357.361
• Mol file: 171925-21-6.mol

Synonyms:(1S,2S,7S,8R,9S)-Indolizidine-1,2,7,8-tetroltetraacetate

Chemical Property of 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 1S-(1.alpha.,2.beta.,7.alpha.,8.alpha.,8a.alpha.)-

There total 29 articles about 1,2,7,8-Indolizinetetrol, octahydro-, tetraacetate (ester), 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: 70.0%

(1S,2R,7R,8R,8aR)-1,2,7,8-tetraacetoxyindolizin-5-one (545427-27-8) → (1S,2R,7R,8R,8aR)-1,2,7,8-tetraacetoxyindolizine (545427-28-9,171925-21-6)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

Reference yield: 61.0%

(1S,2R,7S,8S,8aR)-1,2,7,8-tetraacetoxyindolizin-5-one (149913-61-1) → (1S,2R,7S,8S,8aR)-1,2,7,8-tetraacetoxyindolizine (545427-25-6,171925-21-6)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

Reference yield:

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8) → 1,2,7,8-tetra-O-acetyl-1(R),2(S),7(S),8(R),8a(R)-tetrahydroxyoctahydroindolizidine (171925-21-6)

Guidance literature:

Multi-step reaction with 3 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: H₂ / 20percent Pd(OH)2/C / acetic acid / 16 h

3: pyridine

With pyridine; 1-thiopropane; tetrabutylammomium bromide; hydrogen; lithium hydride; di(n-butyl)tin oxide; palladium dihydroxide; In acetic acid;

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

upstream raw materials:

acetic anhydride

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

1,6,7-tri-O-benzoylcastanospermine

1,2,7-tri-O-benzoyl-1(R),2(S),7(S),8(R),8a(R)-tetrahydroxyoctahydroindolizidine