Technology Process of (1R,6R,11aS,13S,14aR)-6-[2-(benzyloxy)ethyl]-1,13-dihydroxy-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
There total 17 articles about (1R,6R,11aS,13S,14aR)-6-[2-(benzyloxy)ethyl]-1,13-dihydroxy-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:
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1446489-27-5
(1R,6R,11aS,13S,14aR)-6-[2-(benzyloxy)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
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1446489-29-7
(1R,6R,11aS,13S,14aR)-6-[2-(benzyloxy)ethyl]-1,13-dihydroxy-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
- Guidance literature:
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With
triethylamine tris(hydrogen fluoride);
In
acetonitrile;
at 60 ℃;
for 17h;
DOI:10.1021/jm400615g
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1446489-29-7
(1R,6R,11aS,13S,14aR)-6-[2-(benzyloxy)ethyl]-1,13-dihydroxy-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
- Guidance literature:
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Multi-step reaction with 9 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: 0.33 h / 0 °C / Inert atmosphere
8.1: silver(l) oxide; tetra-(n-butyl)ammonium iodide / 7 h / 20 °C
9.1: triethylamine tris(hydrogen fluoride) / acetonitrile / 17 h / 60 °C
With
pyridine; methanol; hexaammonium heptamolybdate tetrahydrate; palladium di-μ-chlorobis (η-allyl); dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; triethylamine tris(hydrogen fluoride); 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; silver(l) oxide;
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
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1446489-29-7
(1R,6R,11aS,13S,14aR)-6-[2-(benzyloxy)ethyl]-1,13-dihydroxy-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 3 h / 20 °C
2.1: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C
3.1: potassium hexamethylsilazane / toluene; 1,2-dimethoxyethane / 18 h / -78 - 20 °C
4.1: potassium hydrogencarbonate; palladium di-μ-chlorobis (η-allyl) / water; N,N-dimethyl-formamide / 3 h / 20 °C
5.1: methanol; sodium hydroxide / tetrahydrofuran / 1 h / 60 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0.08 h / 70 °C / Inert atmosphere
6.2: 0.33 h / 0 °C / Inert atmosphere
7.1: silver(l) oxide; tetra-(n-butyl)ammonium iodide / 7 h / 20 °C
8.1: triethylamine tris(hydrogen fluoride) / acetonitrile / 17 h / 60 °C
With
methanol; potassium osmate(VI) dihydrate; sodium periodate; palladium di-μ-chlorobis (η-allyl); tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine tris(hydrogen fluoride); 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; silver(l) oxide;
In
tetrahydrofuran; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
6.1: |Suzuki-Miyaura Coupling / 6.2: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm400615g