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

Base Information

Chemical Name:(1S,4R,5R)-4-(2-hydroxy-2-methyl-12-phenyldodecyl)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-one
CAS No.:1353566-51-4
Molecular Formula:C₂₄H₃₆O₄
Molecular Weight:388.547
Hs Code.:

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

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

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

There total 24 articles about (1S,4R,5R)-4-(2-hydroxy-2-methyl-12-phenyldodecyl)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-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: 34.0%

: 1353566-43-4
(2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate

: 162559-02-6
(+)-plakortolide E

: 1353566-51-4
(1S,4R,5R)-4-(2-hydroxy-2-methyl-12-phenyldodecyl)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-one

: 4,6-dimethyl-4-hydroxy-3,6-peroxy-16-phenylhexadecanoic acid 1,4-lactone

Guidance literature:: (2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 3h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 2,2,2-trifluoroethanol; at 0 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol203185f

Reference yield: 29.0%

: 1353566-43-4
(2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate

: 162559-02-6
(+)-plakortolide E

: 1353566-51-4
(1S,4R,5R)-4-(2-hydroxy-2-methyl-12-phenyldodecyl)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-one

: 1353566-52-5
C₃₀H₅₀O₄Si

: 4,6-dimethyl-4-hydroxy-3,6-peroxy-16-phenylhexadecanoic acid 1,4-lactone

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20 ℃; for 8h; Inert atmosphere;
DOI:10.1021/ol203185f

Reference yield:

: 1353566-44-5
(R)-2-methyl-4-methylene-14-phenyl-2-((triethylsilyl)oxy)tetradecanal

: 162559-02-6
(+)-plakortolide E

: 1353566-51-4
(1S,4R,5R)-4-(2-hydroxy-2-methyl-12-phenyldodecyl)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-one

: 4,6-dimethyl-4-hydroxy-3,6-peroxy-16-phenylhexadecanoic acid 1,4-lactone

Guidance literature:: Multi-step reaction with 5 steps

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

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

2.2: 20 °C / Inert atmosphere

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

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

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 0 °C

5.2: 3 h / 0 °C / Inert atmosphere

With titanium(IV) isopropylate; dmap; bis(2,2,6,6-tetramethylheptane-3,5-dione)cobalt(II); tetrabutyl ammonium fluoride; oxygen; titanium tetrachloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 1.1: Mukaiyama aldol addition;
DOI:10.1021/ol203185f