(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

Base Information

Chemical Name:(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one
CAS No.:646030-67-3
Molecular Formula:C₄₁H₆₂O₅Si
Molecular Weight:663.026
Hs Code.:

(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

Synonyms:(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

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Chemical Property of (1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

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Technology Process of (1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

There total 21 articles about (1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-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: 55.0%

: 646030-66-2
(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-methoxymethoxy-6,13,19-trimethyl-9-propyl-8,20-dioxabicyclo[15.2.1]eicosane-7,11-dione

: 646030-67-3
(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

Guidance literature:: With titanium tetrachloride; In tetrahydrofuran; Heating;
DOI:10.1021/ja038216z

Reference yield:

: 61540-30-5
3-oxohexanoic acid tert-butyl ester

: 646030-67-3
(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 83 percent / H₂ / [((R)-Binap)-RuCl₂]2(NEt₃) / tetrahydrofuran; methanol / 17 h / 90 - 95 °C / 7500.6 Torr

2.1: 87 percent / DMAP; EDCl / CH₂Cl₂ / 16 h / 20 °C

3.1: 100 percent / Et₃SiH; trifluoroacetic acid / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 100 percent / (COCl)2; DMF / CH₂Cl₂

5.1: Zn-Cu; DMA; TMSCl / toluene / 50 °C

5.2: 84 mg / Pd₂(dba)3; P(furyl)3 / toluene

6.1: 63 percent / ruthenium second generation Grubbs catalyst / toluene / 0.17 h / Heating

7.1: 99 percent / H₂ / Pd/C / ethyl acetate / 760 Torr

8.1: 55 percent / TiCl₄ / tetrahydrofuran / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; dmap; chloro-trimethyl-silane; oxalyl dichloride; hydrogen; titanium tetrachloride; 2,4-dichlorophenoxyacetic acid dimethylamine; copper; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; trifluoroacetic acid; zinc; palladium on activated charcoal; [((R)-Binap)-RuCl₂]2; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; 8.1: Takai olefination;
DOI:10.1021/ja038216z

Reference yield:

: 3249-68-1
ethyl butyroyl acetate

: 646030-67-3
(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 59 percent / t-BuOK / benzene / 144 h / Heating

2.1: 83 percent / H₂ / [((R)-Binap)-RuCl₂]2(NEt₃) / tetrahydrofuran; methanol / 17 h / 90 - 95 °C / 7500.6 Torr

3.1: 87 percent / DMAP; EDCl / CH₂Cl₂ / 16 h / 20 °C

4.1: 100 percent / Et₃SiH; trifluoroacetic acid / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 100 percent / (COCl)2; DMF / CH₂Cl₂

6.1: Zn-Cu; DMA; TMSCl / toluene / 50 °C

6.2: 84 mg / Pd₂(dba)3; P(furyl)3 / toluene

7.1: 63 percent / ruthenium second generation Grubbs catalyst / toluene / 0.17 h / Heating

8.1: 99 percent / H₂ / Pd/C / ethyl acetate / 760 Torr

9.1: 55 percent / TiCl₄ / tetrahydrofuran / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; dmap; chloro-trimethyl-silane; oxalyl dichloride; potassium tert-butylate; hydrogen; titanium tetrachloride; 2,4-dichlorophenoxyacetic acid dimethylamine; copper; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; trifluoroacetic acid; zinc; palladium on activated charcoal; [((R)-Binap)-RuCl₂]2; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; benzene; 9.1: Takai olefination;
DOI:10.1021/ja038216z