(2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione

Base Information

• Chemical Name: (2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione
• CAS No.: 1400145-16-5
• Molecular Formula: C₂₈H₃₅NO₄Si
• Molecular Weight: 477.676
• Mol file: 1400145-16-5.mol

Synonyms:(2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione

Chemical Property of (2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione

There total 4 articles about (2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione 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: 41.0%

phenyl acrylate (937-41-7) + (3S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizine-5,8-dione (181705-73-7) → (2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione (1400145-16-5) + (2R,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione (1400145-23-4)

Guidance literature:

phenyl acrylate; (3S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizine-5,8-dione; With samarium diiodide; zinc amalgam; lithium iodide; In tetrahydrofuran; at 20 ℃; for 9h;

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at 20 ℃; for 9h; stereoselective reaction;

DOI:10.1021/jo3014484

Reference yield:

(3S,8aS)-3-((tert-butyldiphenylsilyloxy)methyl)-8-hydroxyhexahydroindolizin-5(1H)-one (1400145-11-0) → (2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione (1400145-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C / Molecular sieve

2.1: lithium iodide; samarium diiodide; zinc amalgam / tetrahydrofuran / 9 h / 20 °C

2.2: 9 h / 20 °C

With samarium diiodide; tetrapropylammonium perruthennate; zinc amalgam; 4-methylmorpholine N-oxide; lithium iodide; In tetrahydrofuran; dichloromethane; 1.1: |Ley Oxidation;

DOI:10.1021/jo3014484

Reference yield:

(3S,8aS)-3-((tert-butyldiphenylsilyloxy)methyl)-8-hydroxyhexahydroindolizin-5(1H)-one → (2S,3′S,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)tetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione (1400145-16-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium methylate / methanol / 2 h / 0 °C

2.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C / Molecular sieve

3.1: lithium iodide; samarium diiodide; zinc amalgam / tetrahydrofuran / 9 h / 20 °C

3.2: 9 h / 20 °C

With samarium diiodide; tetrapropylammonium perruthennate; zinc amalgam; sodium methylate; 4-methylmorpholine N-oxide; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; 2.1: |Ley Oxidation;

DOI:10.1021/jo3014484

upstream raw materials:

(3S,8aS)-3-((tert-butyldiphenylsilyloxy)methyl)-8-hydroxyhexahydroindolizin-5(1H)-one

phenyl acrylate

(3S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizine-5,8-dione

Downstream raw materials:

(2S,3″S,4R,8a′S)-3′-((tert-butyldiphenylsilyloxy)methyl)-4-methyltetrahydro-1′H,3H-spiro[furan-2,8′-indolizine]-5,5′(4H,8a′H)dione