(1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Base Information

Chemical Name:(1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
CAS No.:1446488-98-7
Molecular Formula:C₂₃H₃₀O₄
Molecular Weight:370.489
Hs Code.:

Synonyms:(1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

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Chemical Property of (1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

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Technology Process of (1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

There total 16 articles about (1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-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: 85.0%

: 1446488-88-5
(1R,6R,11aS,13S,14aR)-1,13-bis{[tert-butyl(dimethyl)silyl]oxy}-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

: 1446488-98-7
(1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Guidance literature:: With triethylamine tris(hydrogen fluoride); In acetonitrile; at 60 ℃; for 15h;
DOI:10.1021/jm400615g

Reference yield:

: 177960-81-5
(1R,2E,6S,10E,11aS,13S,14aR)-1,13-bis[(tert-butyldimethylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f][1]oxacyclotridecin-4-one

: 1446488-98-7
(1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium hydroxide / methanol; water / 0.5 h / 40 °C

1.2: 20 °C

2.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 3 h / 20 °C

3.1: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C

4.1: potassium hexamethylsilazane / toluene; 1,2-dimethoxyethane / 18 h / -78 - 20 °C

5.1: potassium hydrogencarbonate; palladium di-μ-chlorobis (η-allyl) / water; N,N-dimethyl-formamide / 3 h / 20 °C

6.1: methanol; sodium hydroxide / tetrahydrofuran / 1 h / 60 °C

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0.08 h / 70 °C / Inert atmosphere

7.2: 20 h / Inert atmosphere

8.1: triethylamine tris(hydrogen fluoride) / acetonitrile / 15 h / 60 °C

With methanol; potassium osmate(VI) dihydrate; sodium periodate; palladium di-μ-chlorobis (η-allyl); potassium hexamethylsilazane; potassium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine tris(hydrogen fluoride); 9-bora-bicyclo[3.3.1]nonane; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 7.1: |Suzuki-Miyaura Coupling / 7.2: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm400615g

Reference yield:

: 1446488-81-8
ethyl (2E)-7-[(1-Phenyl-1H-tetrazol-5-yl)thio]hept-2-enoate

: 1446488-98-7
(1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-phenylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / -78 °C

2.1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.1: dihydrogen peroxide; hexaammonium heptamolybdate tetrahydrate / ethanol / 16 h / 0 - 20 °C

4.1: potassium hexamethylsilazane / toluene; 1,2-dimethoxyethane / 18 h / -78 - 20 °C

5.1: potassium hydrogencarbonate; palladium di-μ-chlorobis (η-allyl) / water; N,N-dimethyl-formamide / 3 h / 20 °C

6.1: methanol; sodium hydroxide / tetrahydrofuran / 1 h / 60 °C

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0.08 h / 70 °C / Inert atmosphere

7.2: 20 h / Inert atmosphere

8.1: triethylamine tris(hydrogen fluoride) / acetonitrile / 15 h / 60 °C

With pyridine; methanol; hexaammonium heptamolybdate tetrahydrate; palladium di-μ-chlorobis (η-allyl); dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; triethylamine tris(hydrogen fluoride); 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: |Suzuki-Miyaura Coupling / 7.2: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm400615g