(1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene

Base Information

Chemical Name:(1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene
CAS No.:1269249-92-4
Molecular Formula:C₂₄H₃₄O₄
Molecular Weight:386.532
Hs Code.:

Synonyms:(1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene

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Chemical Property of (1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene

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Technology Process of (1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene

There total 3 articles about (1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene 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: 70.0%

: 1269249-90-2
(1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane

: 1269249-92-4
(1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene

Guidance literature:: (1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane; With oxygen; methylene blue; In methanol; at 20 - 25 ℃; for 9h; Irradiation; sealed tube; Inert atmosphere;

With triphenylphosphine; In methanol; diethyl ether; at 20 ℃; for 12h; Inert atmosphere;

With dihydrogen peroxide; In methanol; diethyl ether; water; at 20 ℃; for 1.5h; regioselective reaction; Inert atmosphere;
DOI:10.1021/jo200075v

Reference yield:

: 1269250-30-7
C₁₇H₂₆O₃

: 1269249-92-4
(1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / methanol; ethanol / 3 h / 0 - 20 °C / Inert atmosphere

2.1: magnesium oxide / 1,1-dichloroethane / 8 h / 80 °C / Inert atmosphere

3.1: oxygen; methylene blue / methanol / 9 h / 20 - 25 °C / Irradiation; sealed tube; Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

3.3: 1.5 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; oxygen; methylene blue; magnesium oxide; In methanol; 1,1-dichloroethane; ethanol;
DOI:10.1021/jo200075v

Reference yield:

: 1269249-88-8
(1S,2R,5S)-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octan-2-ol

: 1269249-92-4
(1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: magnesium oxide / 1,1-dichloroethane / 8 h / 80 °C / Inert atmosphere

2.1: oxygen; methylene blue / methanol / 9 h / 20 - 25 °C / Irradiation; sealed tube; Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

2.3: 1.5 h / 20 °C / Inert atmosphere

With oxygen; methylene blue; magnesium oxide; In methanol; 1,1-dichloroethane;
DOI:10.1021/jo200075v