(1S,6R,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone

Base Information

• Chemical Name: (1S,6R,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone
• CAS No.: 146987-12-4
• Molecular Formula: C₂₆H₄₀N₂O₅SSi
• Molecular Weight: 520.766
• Mol file: 146987-12-4.mol

Synonyms:

Chemical Property of (1S,6R,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6R,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone

There total 3 articles about (1S,6R,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone 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:

4-<(tert-butyldimethylsilyl)oxy>-3,4-dihydro-5-methyl-2H-pyrrole (126645-93-0) → (1S,6R,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (146987-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -25 deg C, 30 min, 2.) THF, -25 deg C, 1.5 h

2: 1.) n-BuLi / 1.) THF/hexane, -78 deg C, 10 min, 2.) benzene, 22 deg C, 6 h

With n-butyllithium; lithium diisopropyl amide;

DOI:10.1021/jo00060a034

Reference yield:

(-)-menthyl p-toluenesulfinate (1517-82-4) → (1S,6R,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (146987-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -25 deg C, 30 min, 2.) THF, -25 deg C, 1.5 h

2: 1.) n-BuLi / 1.) THF/hexane, -78 deg C, 10 min, 2.) benzene, 22 deg C, 6 h

With n-butyllithium; lithium diisopropyl amide;

DOI:10.1021/jo00060a034

Reference yield:

methyl 2-[(tert-butoxycarbonyl)amino]acrylate (55477-80-0) + (3S,SR)-3-<(tert-butyldimethylsilyl)oxy>-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole (146955-02-4) → (1S,6S,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (146955-16-0) + (1S,6R,SS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7-hexahydro-8-<(4-methylphenyl)sulfinyl>-5-indolizinone (146987-12-4)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF/hexane, -78 deg C, 10 min, 2.) benzene, 22 deg C, 6 h;

DOI:10.1021/jo00060a034

upstream raw materials:

methyl 2-[(tert-butoxycarbonyl)amino]acrylate

(3S,SR)-3-<(tert-butyldimethylsilyl)oxy>-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole

4-<(tert-butyldimethylsilyl)oxy>-3,4-dihydro-5-methyl-2H-pyrrole

(-)-menthyl p-toluenesulfinate

Downstream raw materials:

(-)-slaframine

(1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine

(1S,6R,8aS)-6-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone