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

Base Information

• Chemical Name: (4R,5R)-4-hydroxy-5-((R)-2-hydroxy-2-methyl-12-phenyldodecyl)-5-methyldihydrofuran-2(3H)-one
• CAS No.: 1353566-42-3
• Molecular Formula: C₂₄H₃₈O₄
• Molecular Weight: 390.563
• Mol file: 1353566-42-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (4R,5R)-4-hydroxy-5-((R)-2-hydroxy-2-methyl-12-phenyldodecyl)-5-methyldihydrofuran-2(3H)-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: 91.0%

(+)-plakortolide E (162559-02-6) → (4R,5R)-4-hydroxy-5-((R)-2-hydroxy-2-methyl-12-phenyldodecyl)-5-methyldihydrofuran-2(3H)-one (1353566-42-3)

Guidance literature:

With acetic acid; zinc; In diethyl ether; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ol203185f

Reference yield:

1 ,6-dibromohexane (629-03-8) → (4R,5R)-4-hydroxy-5-((R)-2-hydroxy-2-methyl-12-phenyldodecyl)-5-methyldihydrofuran-2(3H)-one (1353566-42-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: magnesium / tetrahydrofuran / Inert atmosphere

1.2: 16 h / -10 - 20 °C / Inert atmosphere

2.1: magnesium / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2.2: 18 h / 0 - 4 °C / Inert atmosphere

3.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.17 h / -25 °C / Inert atmosphere

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

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

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

6.2: -50 - 20 °C / Inert atmosphere

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

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

8.2: 20 °C / Inert atmosphere

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

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

11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 0 °C

11.2: 3 h / 0 °C / Inert atmosphere

12.1: acetic acid; zinc / diethyl ether / 20 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; dmap; oxalyl dichloride; bis(2,2,6,6-tetramethylheptane-3,5-dione)cobalt(II); tetrabutyl ammonium fluoride; tert.-butyl lithium; oxygen; silica gel; titanium tetrachloride; magnesium; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; Petroleum ether; pentane; 6.1: Swern oxidation / 6.2: Swern oxidation / 7.1: 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) → (4R,5R)-4-hydroxy-5-((R)-2-hydroxy-2-methyl-12-phenyldodecyl)-5-methyldihydrofuran-2(3H)-one (1353566-42-3)

Guidance literature:

Multi-step reaction with 9 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

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 0 °C

8.2: 3 h / 0 °C / Inert atmosphere

9.1: acetic acid; zinc / diethyl ether / 20 h / 20 °C / Inert atmosphere

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; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; 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:

1 ,6-dibromohexane

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

(R)-3,3,8,8-tetraethyl-5-methyl-5-(2-methylene-12-phenyldodecyl)-4,7-dioxa-3,8-disiladecane

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

Downstream raw materials:

(S)-(2R,3R)-2-[(R)-2-hydroxy-2-methyl-12-phenyldodecyl]-2-methyl-5-oxotetrahydrofuran-3-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

(R)-(2R,3R)-2-[(R)-2-hydroxy-2-methyl-12-phenyldodecyl]-2-methyl-5-oxotetrahydrofuran-3-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

(S)-(2R,3R)-2-[(R)-2-hydroxy-2-methyl-12-phenyldodecyl]-2-methyl-5-oxotetrahydrofuran-3-yl 2-methoxy-2-phenylacetate

(R)-(2R,3R)-2-[(R)-2-hydroxy-2-methyl-12-phenyldodecyl]-2-methyl-5-oxotetrahydrofuran-3-yl 2-methoxy-2-phenylacetate