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

Base Information

• Chemical Name: (1S,6S,9R,13R,17R,19S)-(+)-15-tert-butyldiphenylsilyloxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7,14-dione
• CAS No.: 501015-62-9
• Molecular Formula: C₄₁H₆₀O₅Si
• Molecular Weight: 661.01
• Mol file: 501015-62-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (1S,6S,9R,13R,17R,19S)-(+)-15-tert-butyldiphenylsilyloxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7,14-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: 83.0%

(1S,6S,9R,13R,14S,17R,19S)-(+)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one (501015-65-2) → (1S,6S,9R,13R,17R,19S)-(+)-15-tert-butyldiphenylsilyloxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7,14-dione (501015-62-9)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1002/anie.200290042

Reference yield:

(E/Z)-(1S,6S,9R,13R,14S,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-methoxymethoxy-6,13,19-trimethyl-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-3-en-7,11-dione → (1S,6S,9R,13R,17R,19S)-(+)-15-tert-butyldiphenylsilyloxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7,14-dione (501015-62-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760 Torr

2: 64 percent / TiCl₄ / tetrahydrofuran / 2 h / Heating

3: 85 percent / Bu₄NBr; TMSCl / CH₂Cl₂ / 5 °C

4: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h

With chloro-trimethyl-silane; tetrabutylammomium bromide; hydrogen; titanium tetrachloride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 2: Takai olefination / 4: Dess-Martin oxidation;

DOI:10.1021/ja038216z

Reference yield:

(1S,6S,9R,13R,14S,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-methoxymethoxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one (501015-61-8) → (1S,6S,9R,13R,17R,19S)-(+)-15-tert-butyldiphenylsilyloxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7,14-dione (501015-62-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Bu₄NBr; TMSCl / CH₂Cl₂ / 5 °C

2: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h

With chloro-trimethyl-silane; tetrabutylammomium bromide; Dess-Martin periodane; In dichloromethane; 2: Dess-Martin oxidation;

DOI:10.1021/ja038216z

upstream raw materials:

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

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