(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Base Information

Chemical Name:(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene
CAS No.:199122-64-0
Molecular Formula:C₂₃H₃₂O₃
Molecular Weight:356.505
Hs Code.:

Synonyms:(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

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Chemical Property of (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

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Technology Process of (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

There total 8 articles about (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-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: 95.0%

: 100-39-0
benzyl bromide

: 199122-44-6
(1S,2R)-2-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-cyclohexanol

: 199122-64-0
(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja971881l

Reference yield:

: 153380-53-1
(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde

: 199122-64-0
(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

2.1: 99 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

3.1: 83 percent / MgBr₂*Et₂O; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

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

4.2: 95 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

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

Reference yield:

: 90719-37-2
(4S,1'R,2'R,3'S,4'S)-3-[(3'-methylbicyclo[2.2.1]hept-5'-ene-2'-yl)carbonyl]-4-iso-propyloxazolidin-2-one

: 199122-64-0
(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-cyclohexyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2.1: 73 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

3.1: 93 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

4.1: 99 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

5.1: 83 percent / MgBr₂*Et₂O; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

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

6.2: 95 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; magnesium bromide; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Swern oxidation;
DOI:10.1016/S0040-4020(00)00859-0