((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol

Base Information

• Chemical Name: ((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol
• CAS No.: 1392104-50-5
• Molecular Formula: C₁₉H₂₅N₃O₄
• Molecular Weight: 359.425
• Mol file: 1392104-50-5.mol

Synonyms:((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol

Chemical Property of ((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol

There total 13 articles about ((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol 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: 99.0%

4-((2S,6S,8S)-8-((tert-butyldiphenylsilyloxy)methyl)-1,7-dioxaspiro[5.5]undecan-2-yl)-1-(3-methoxyphenyl)-1H-1,2,3-triazole (1392104-48-1) → ((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol (1392104-50-5)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 20 ℃; for 48h; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c2ob06802h

Reference yield:

11(S)-(tert-butyldimethylsilyloxy)-12-(tert-butyldiphenylsilyloxy)-7-(1,3-dioxolan-2-yl)dodec-1-yn-(3)-ol → ((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol (1392104-50-5)

Guidance literature:

Multi-step reaction with 5 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

5: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

With borane Ν,Ν-diethylaniline complex; triethylphosphite copper(I) iodide complex; camphor-10-sulfonic acid; triethylamine tris(hydrogen fluoride); (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:

6-(tert-butyldiphenylsilyloxy)-(5S)-5-hydroxyl-N-methoxy-N-methylhexanamide (1392104-16-3) → ((2S,6S,8S)-8-(1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methanol (1392104-50-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole; dmap / dichloromethane / 13 h / 20 - 45 °C / Inert atmosphere

2.1: iodine; magnesium / diethyl ether / Inert atmosphere

2.2: 3 h / 0 °C / Inert atmosphere

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

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

4.2: 0.5 h / -78 - 20 °C / Inert atmosphere

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

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

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

8.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

With bismuth(lll) trifluoromethanesulfonate; 1H-imidazole; dmap; triethylphosphite copper(I) iodide complex; camphor-10-sulfonic acid; iodine; sodium hydrogencarbonate; ozone; magnesium; triethylamine tris(hydrogen fluoride); 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

3-methoxyphenyl azide

8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

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

Refernces