(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

Base Information

Chemical Name:(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
CAS No.:1446489-27-5
Molecular Formula:C₃₆H₆₀O₅Si₂
Molecular Weight:629.04
Hs Code.:

(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

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 17 articles about (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 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: 65.0%

: 1446489-24-2
(1R,6R,11aS,13S,14aR)-1,13-bis{[tert-butyl(dimethyl)silyl]oxy}-6-(2-hydroxyethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

: 100-39-0
benzyl bromide

: 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

Guidance literature:: With tetra-(n-butyl)ammonium iodide; silver(l) oxide; at 20 ℃; for 7h;
DOI:10.1021/jm400615g

Reference yield:

: 1446488-71-6
methyl (2E,4R)-4-[(tert-butyldimethylsilyl)oxy]-4-{(1'R,2'S,4'S)-4'-[(tert-butyldimethylsilyl)oxy]-2'-[(1''E,6''S)-6''-hydroxyhept-1''-en-1''-yl]cyclopentyl}but-2-enoate

: 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

Guidance literature:: Multi-step reaction with 7 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

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; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; silver(l) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; acetone; toluene; 6.1: |Suzuki-Miyaura Coupling / 6.2: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm400615g

Reference yield:

: 1446488-72-7
methyl (2E,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-4-((1R,2R,4R)-4-{[tert-butyl(dimethyl)-silyl]oxy}-2-formylcyclopentyl)but-2-enoate

: 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

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0.08 h / 70 °C / Inert atmosphere

4.2: 0.33 h / 0 °C / Inert atmosphere

5.1: silver(l) oxide; tetra-(n-butyl)ammonium iodide / 7 h / 20 °C

With methanol; palladium di-μ-chlorobis (η-allyl); tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium hydrogencarbonate; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; silver(l) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; toluene; 4.1: |Suzuki-Miyaura Coupling / 4.2: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm400615g