(2S,3aS,6aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-tetrahydro-cyclopenta[1,3]dioxole

Base Information

Chemical Name:(2S,3aS,6aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-tetrahydro-cyclopenta[1,3]dioxole
CAS No.:199122-20-8
Molecular Formula:C₁₄H₂₀O₂
Molecular Weight:220.312
Hs Code.:

Synonyms:(2S,3aS,6aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-tetrahydro-cyclopenta[1,3]dioxole

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3aS,6aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-tetrahydro-cyclopenta[1,3]dioxole

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Technology Process of (2S,3aS,6aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-tetrahydro-cyclopenta[1,3]dioxole

There total 1 articles about (2S,3aS,6aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-tetrahydro-cyclopenta[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: 93.0%

: 5057-98-7,86703-52-8
cis-1,2-cyclopentanediol

: 199122-67-3
(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclopentyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

: 137765-98-1
(1R,2S)-2-Benzyloxy-cyclopentanol

: 199122-20-8
(2S,3aS,6aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-tetrahydro-cyclopenta[1,3]dioxole

Guidance literature:: With pyridinium p-toluenesulfonate; In benzene; Ambient temperature;
DOI:10.1021/ja971881l

Reference yield:

: 199122-20-8
(2S,3aS,6aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-tetrahydro-cyclopenta[1,3]dioxole

: 199122-67-3
(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclopentyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

2.1: 86 percent / MgBr₂*Et₂O; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

3.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 20 °C

3.2: 93 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; sodium hydride; magnesium bromide; zinc; In tetrahydrofuran; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(00)00859-0