(5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one

Base Information

• Chemical Name: (5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one
• CAS No.: 1315277-80-5
• Molecular Formula: C₃₅H₄₄O₄Si
• Molecular Weight: 556.817

Synonyms:(5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one

Chemical Property of (5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one

Chemical Property:

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Technology Process of (5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one

There total 12 articles about (5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-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: 54.0%

C35H44O4Si → (5S,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one (1338070-51-1) + (5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one (1315277-80-5)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 3.2h; Inert atmosphere; Darkness;

DOI:10.1016/j.tet.2011.03.114

Reference yield:

C15H20O3 (1315278-14-8) → (5S,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one (1338070-51-1) + (5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one (1315277-80-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrahydrofuran / 1.2 h / 20 °C / Inert atmosphere

2.1: dihydrogen peroxide; sodium hydrogencarbonate / tetrahydrofuran; water / 2 h / 0 °C

3.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

3.2: 0.67 h / 0 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / hexane; dichloromethane / 2.2 h / -78 - 0 °C / Inert atmosphere

4.2: 0.67 h / 0 - 20 °C

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 1.2 h / 0 - 20 °C

6.2: 0 °C

7.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

8.1: copper(l) iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; trifuran-2-yl-phosphane; triethylamine / N,N-dimethyl-formamide / 4.4 h / 50 °C / Inert atmosphere

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / pH 7 / buffer

10.1: silver trifluoromethanesulfonate / dichloromethane / 3.2 h / 20 °C / Inert atmosphere; Darkness

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; trifuran-2-yl-phosphane; potassium tert-butylate; dihydrogen peroxide; silver trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tet.2011.03.114

Reference yield:

C27H43BO3 → (5S,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one (1338070-51-1) + (5R,6R)-6-(3-benzyloxypropyl)-2-[3-(tert-butyldiphenylsilyloxy)propyl]-5-methyl-5,6-dihydro-4H-pyran-4-one (1315277-80-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: dihydrogen peroxide; sodium hydrogencarbonate / tetrahydrofuran; water / 2 h / 0 °C

2.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

2.2: 0.67 h / 0 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 2.2 h / -78 - 0 °C / Inert atmosphere

3.2: 0.67 h / 0 - 20 °C

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 1.2 h / 0 - 20 °C

5.2: 0 °C

6.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

7.1: copper(l) iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; trifuran-2-yl-phosphane; triethylamine / N,N-dimethyl-formamide / 4.4 h / 50 °C / Inert atmosphere

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / pH 7 / buffer

9.1: silver trifluoromethanesulfonate / dichloromethane / 3.2 h / 20 °C / Inert atmosphere; Darkness

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; trifuran-2-yl-phosphane; potassium tert-butylate; dihydrogen peroxide; silver trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tet.2011.03.114

upstream raw materials:

(2S,3R)-1-((4-methoxybenzyl)oxy)-2-methylhex-5-en-3-ol

C₂₉H₃₄O₄S

C₁₅H₂₀O₃

C₁₅H₂₂O₄

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