(2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate

Base Information

• Chemical Name: (2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate
• CAS No.: 1353566-43-4
• Molecular Formula: C₃₂H₅₄O₆Si
• Molecular Weight: 562.863
• Mol file: 1353566-43-4.mol

Synonyms:(2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate

Chemical Property of (2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate

There total 11 articles about (2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate 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: 94.0%

triethylsilane (617-86-7) + (2R,3R)-2-methyl-2-(2-methylene-12-phenyldodecyl)-5-oxotetrahydrofuran-3-yl acetate (1353566-50-3) → (2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate (1353566-43-4)

Guidance literature:

With bis(2,2,6,6-tetramethylheptane-3,5-dione)cobalt(II); oxygen; In 1,2-dichloro-ethane; at 20 ℃; for 2h; regioselective reaction;

DOI:10.1021/ol203185f

Reference yield:

(R)-2-methyl-4-methylene-14-phenyl-2-((triethylsilyl)oxy)tetradecan-1-ol (1353566-48-9) → (2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate (1353566-43-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -70 - -50 °C / Inert atmosphere

1.2: -50 - 20 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -78 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: bis(2,2,6,6-tetramethylheptane-3,5-dione)cobalt(II); oxygen / 1,2-dichloro-ethane / 2 h / 20 °C

With titanium(IV) isopropylate; dmap; oxalyl dichloride; bis(2,2,6,6-tetramethylheptane-3,5-dione)cobalt(II); tetrabutyl ammonium fluoride; oxygen; titanium tetrachloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Mukaiyama aldol addition;

DOI:10.1021/ol203185f

Reference yield:

(R)-2-methyl-4-methylene-14-phenyl-1-((triethylsilyl)oxy)tetradecan-2-ol (1353566-47-8) → (2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate (1353566-43-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: silica gel / diethyl ether; Petroleum ether / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -70 - -50 °C / Inert atmosphere

3.2: -50 - 20 °C / Inert atmosphere

4.1: titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -78 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: bis(2,2,6,6-tetramethylheptane-3,5-dione)cobalt(II); oxygen / 1,2-dichloro-ethane / 2 h / 20 °C

With titanium(IV) isopropylate; dmap; oxalyl dichloride; bis(2,2,6,6-tetramethylheptane-3,5-dione)cobalt(II); tetrabutyl ammonium fluoride; oxygen; silica gel; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; Petroleum ether; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Mukaiyama aldol addition;

DOI:10.1021/ol203185f

upstream raw materials:

triethylsilane

(2R,3R)-2-methyl-2-(2-methylene-12-phenyldodecyl)-5-oxotetrahydrofuran-3-yl acetate

1 ,6-dibromohexane

(R)-2-methyl-4-methylene-14-phenyl-1-((triethylsilyl)oxy)tetradecan-2-ol

Downstream raw materials:

(+)-plakortolide E

(1S,4R,5R)-4-(2-hydroxy-2-methyl-12-phenyldodecyl)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-one

C₃₀H₅₀O₄Si

(4R,5R)-4-hydroxy-5-((R)-2-hydroxy-2-methyl-12-phenyldodecyl)-5-methyldihydrofuran-2(3H)-one