11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one

Base Information

• Chemical Name: 11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one
• CAS No.: 1392104-38-9
• Molecular Formula: C₃₉H₅₇N₃O₄Si
• Molecular Weight: 659.985
• Mol file: 1392104-38-9.mol

Synonyms:

Chemical Property of 11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one

There total 12 articles about 11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one 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:

11(S)-(tert-butyldimethylsilyloxy)-12-(tert-butyldiphenylsilyloxy)-7-(1,3-dioxolan-2-yl)dodec-1-yn-(3)-ol → 11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one (1392104-38-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 - 40 °C

2: borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere

3: camphor-10-sulfonic acid / ethanol; water / 3 h / 20 °C

4: triethylphosphite copper(I) iodide complex / toluene / Inert atmosphere; Reflux

With borane Ν,Ν-diethylaniline complex; triethylphosphite copper(I) iodide complex; camphor-10-sulfonic acid; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; toluene;

DOI:10.1039/c2ob06802h

Reference yield:

(3S,11S)-11-(tert-butyldimethylsilyloxy)-12-(tert-butyldiphenylsilyloxy)-7-(1,3-dioxolan-2-yl)dodec-1-yn-3-yl acetate (1392104-14-1) → 11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one (1392104-38-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / methanol / 0.33 h / 20 °C

2: camphor-10-sulfonic acid / ethanol; water / 3 h / 20 °C

3: triethylphosphite copper(I) iodide complex / toluene / Inert atmosphere; Reflux

With triethylphosphite copper(I) iodide complex; camphor-10-sulfonic acid; potassium carbonate; In methanol; ethanol; water; toluene;

DOI:10.1039/c2ob06802h

Reference yield:

(5S)-5-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylhexanamide (1392104-08-3) → 11-(4-(8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1H-1,2,3-triazol-1-yl)undecan-2-one (1392104-38-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: iodine; magnesium / diethyl ether / Inert atmosphere

1.2: 3 h / 0 °C / Inert atmosphere

2.1: bismuth(lll) trifluoromethanesulfonate; orthoformic acid triethyl ester / toluene / 20 °C

3.1: sodium hydrogencarbonate; ozone; Sudan III / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid / ethanol; water / 3 h / 20 °C

6.1: triethylphosphite copper(I) iodide complex / toluene / Inert atmosphere; Reflux

With bismuth(lll) trifluoromethanesulfonate; triethylphosphite copper(I) iodide complex; camphor-10-sulfonic acid; iodine; sodium hydrogencarbonate; ozone; magnesium; orthoformic acid triethyl ester; Sudan III; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene;

DOI:10.1039/c2ob06802h

upstream raw materials:

(3S,11S)-11-(tert-butyldimethylsilyloxy)-12-(tert-butyldiphenylsilyloxy)-7-(1,3-dioxolan-2-yl)dodec-1-yn-3-yl acetate

6-(tert-butyldiphenylsilyloxy)-(5S)-5-hydroxyl-N-methoxy-N-methylhexanamide

(5S)-5-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylhexanamide

(10S)-10-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)undec-1-en-6-one