(2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1⁽⁶⁾,2-dieno[5,4-d][1,3]dioxole

Base Information

• Chemical Name: (2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1⁽⁶⁾,2-dieno[5,4-d][1,3]dioxole
• CAS No.: 1042952-09-9
• Molecular Formula: C₁₄H₁₃ClO₄
• Molecular Weight: 280.708

Synonyms:(2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1⁽⁶⁾,2-dieno[5,4-d][1,3]dioxole

Chemical Property of (2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1⁽⁶⁾,2-dieno[5,4-d][1,3]dioxole

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Technology Process of (2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1⁽⁶⁾,2-dieno[5,4-d][1,3]dioxole

There total 1 articles about (2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1⁽⁶⁾,2-dieno[5,4-d][1,3]dioxole 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: 75.0%

C14H13ClO3 (1042952-07-7) → (2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1(6),2-dieno[5,4-d][1,3]dioxole (1042952-09-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 18 ℃; for 18h;

DOI:10.1016/j.tet.2008.04.070

Reference yield: 92.0%

(2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1(6),2-dieno[5,4-d][1,3]dioxole (1042952-09-9) → C14H15ClO4 (1072090-12-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -30 - -10 ℃; for 1h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol801815k

Reference yield: 42.0%

(2S,3aS,5aR,6aR,6bS)-4-chloro-3a,5a,6a,6b-tetrahydro-2-(4-methoxyphenyl)-7-oxabicyclo[4.1.0]hepta-1(6),2-dieno[5,4-d][1,3]dioxole (1042952-09-9) → (1R,2S,3S)-3-(4-methoxybenzyloxy)-4-chlorocyclohex-4-ene-1,2-diol (1042952-10-2)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -60 - -30 ℃; for 7h;

DOI:10.1016/j.tet.2008.04.070

upstream raw materials:

C₁₄H₁₃ClO₃

Downstream raw materials:

(1R,2S,3S)-3-(4-methoxybenzyloxy)-4-chlorocyclohex-4-ene-1,2-diol

C₁₄H₁₅ClO₄

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