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

Base Information

• Chemical Name: (1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane
• CAS No.: 1269249-90-2
• Molecular Formula: C₂₄H₃₄O₃
• Molecular Weight: 370.532
• Mol file: 1269249-90-2.mol

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

Chemical Property of (1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane

There total 2 articles about (1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane 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: 76.0%

(1S,2R,5S)-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octan-2-ol (1269249-88-8) + benzyloxypyridinium triflate → dibenzyl ether (103-50-4) + C17H28O3 (1269249-84-4) + (1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane (1269249-90-2)

Guidance literature:

With magnesium oxide; In 1,1-dichloroethane; at 80 ℃; for 8h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/jo200075v

Reference yield:

C17H26O3 (1269250-30-7) → (1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane (1269249-90-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium tetrahydroborate; magnesium oxide; In methanol; 1,1-dichloroethane; ethanol;

DOI:10.1021/jo200075v

Reference yield: 70.0%

(1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane (1269249-90-2) → (1S,5S,8R)-8-benzyloxy-1-ethoxycarbonyl-5,7,7-trimethyl-2-(2-hydroxyprop-2-yl)bicyclo[3.3.0]oct-2-ene (1269249-92-4)

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

upstream raw materials:

C₁₇H₂₆O₃

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

Downstream raw materials:

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

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

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