(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

Base Information

• Chemical Name: (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
• CAS No.: 501015-65-2
• Molecular Formula: C₄₁H₆₂O₅Si
• Molecular Weight: 663.026
• Mol file: 501015-65-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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: 85.0%

(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,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)

Guidance literature:

With chloro-trimethyl-silane; tetrabutylammomium bromide; In dichloromethane; at 0 ℃;

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,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)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/ja038216z

Reference yield:

(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 (501015-60-7) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / TiCl₄ / tetrahydrofuran / 2 h / Heating

2: 85 percent / Bu₄NBr; TMSCl / CH₂Cl₂ / 5 °C

With chloro-trimethyl-silane; tetrabutylammomium bromide; titanium tetrachloride; In tetrahydrofuran; dichloromethane; 1: Takai olefination;

DOI:10.1021/ja038216z

upstream raw materials:

(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

Downstream raw materials:

(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