(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

Base Information

• Chemical Name: (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
• CAS No.: 646030-66-2
• Molecular Formula: C₄₂H₆₄O₇Si
• Molecular Weight: 709.051
• Mol file: 646030-66-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 20 articles about (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 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: 99.0%

(1S,6S,9R,13R,14S,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-methoxymethoxy-6,13,19-trimethyl-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-3-en-7,11-dione → (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 (646030-66-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; under 760 Torr;

DOI:10.1021/ja038216z

Reference yield:

3-oxohexanoic acid tert-butyl ester (61540-30-5) → (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 (646030-66-2)

Guidance literature:

Multi-step reaction with 7 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

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; 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;

DOI:10.1021/ja038216z

Reference yield:

(3R)-hydroxyhexanoic acid tert-butyl ester (137567-99-8) → (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 (646030-66-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 87 percent / DMAP; EDCl / CH₂Cl₂ / 16 h / 20 °C

2.1: 100 percent / Et₃SiH; trifluoroacetic acid / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 100 percent / (COCl)2; DMF / CH₂Cl₂

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

4.2: 84 mg / Pd₂(dba)3; P(furyl)3 / toluene

5.1: 63 percent / ruthenium second generation Grubbs catalyst / toluene / 0.17 h / Heating

6.1: 99 percent / H₂ / Pd/C / ethyl acetate / 760 Torr

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; 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; In dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ja038216z

upstream raw materials:

3-oxohexanoic acid tert-butyl ester

ethyl butyroyl acetate

(3R)-hydroxyhexanoic acid tert-butyl ester

tert-butylchlorodiphenylsilane

Downstream raw materials:

(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

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