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

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Chemical Name:(1S,6R)-6-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-cyclohex-3-enol
CAS No.:329366-20-3
Molecular Formula:C₁₆H₂₄O₃
Molecular Weight:264.365
Hs Code.:

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

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

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

There total 5 articles about (1S,6R)-6-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-cyclohex-3-enol 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: 85.0%

: 215389-08-5
C₁₆H₂₃BrO₃

: 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

Guidance literature:: With zinc(II) chloride; zinc; In N,N-dimethyl acetamide; at 75 ℃; for 12h;
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

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

2: 97 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

3: 85 percent / ZnCl₂; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

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

Reference yield:

: 94668-49-2
(1R,2R,3S,4S)-3-methyl-5-norbornene-2-methanol

: 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

Guidance literature:: Multi-step reaction with 4 steps

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

2: 86 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

3: 97 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

4: 85 percent / ZnCl₂; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; oxalyl dichloride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; zinc(II) chloride; zinc; In dichloromethane; N,N-dimethyl acetamide; toluene; acetonitrile; 1: Swern oxidation;
DOI:10.1016/S0040-4020(00)00859-0