(1S,4R,5R,6S)-5-[(R)-((1R,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

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Chemical Name:(1S,4R,5R,6S)-5-[(R)-((1R,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene
CAS No.:215389-15-4
Molecular Formula:C₂₃H₃₀O₃
Molecular Weight:354.489
Hs Code.:

Synonyms:(1S,4R,5R,6S)-5-[(R)-((1R,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-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,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-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,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

There total 8 articles about (1S,4R,5R,6S)-5-[(R)-((1R,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-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: 99.0%

: 100-39-0
benzyl bromide

: 329366-20-3
(1S,6R)-6-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-cyclohex-3-enol

: 215389-15-4
(1S,4R,5R,6S)-5-[(R)-((1R,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Guidance literature:: (1S,6R)-6-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-cyclohex-3-enol; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1016/S0040-4020(00)00859-0

Reference yield:

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

: 215389-15-4
(1S,4R,5R,6S)-5-[(R)-((1R,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

2.1: 97 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

3.1: 85 percent / ZnCl₂; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

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

4.2: 99 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

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

Reference yield:

: 215389-04-1
(2S,3aS,7aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole

: 215389-15-4
(1S,4R,5R,6S)-5-[(R)-((1R,6S)-6-Benzyloxy-cyclohex-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

2.1: 85 percent / ZnCl₂; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

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

3.2: 99 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

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