(1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol

Base Information

Chemical Name:(1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol
CAS No.:595604-83-4
Molecular Formula:C₂₁H₂₈O₃
Molecular Weight:328.452
Hs Code.:

Synonyms:(1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol

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Chemical Property of (1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol

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Technology Process of (1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol

There total 6 articles about (1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol 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: 65.0%

: 595604-80-1
C₂₁H₂₂O₃

: 595604-83-4
(1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;
DOI:10.1016/S0040-4039(03)01176-6

Reference yield:

: 98919-68-7
(1R,2S)-trans-2-phenylcyclohexanol

: 595604-83-4
(1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / Na₂Cr₂O₇ / H₂O / 0.5 h

2: 93 percent / n-BuLi / 6 h / -10 - 20 °C

3: 74 percent / mCPBA / CH₂Cl₂ / 4 h / 10 °C

4: 95 percent / Jones' reagent / acetone / 0.5 h / 20 °C

5: 90 percent / Et₂AlCl / CH₂Cl₂ / 3 h / 0 °C

6: 65 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

With lithium aluminium tetrahydride; n-butyllithium; jones' reagent; sodium dichromate; diethylaluminium chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water; acetone; 5: Diels-Alder reaction;
DOI:10.1016/S0040-4039(03)01176-6

Reference yield:

: 1444-65-1,34281-93-1,55700-93-1,34281-94-2
(2S)-2-phenyl-1-cyclohexanone

: 595604-83-4
(1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / n-BuLi / 6 h / -10 - 20 °C

2: 74 percent / mCPBA / CH₂Cl₂ / 4 h / 10 °C

3: 95 percent / Jones' reagent / acetone / 0.5 h / 20 °C

4: 90 percent / Et₂AlCl / CH₂Cl₂ / 3 h / 0 °C

5: 65 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

With lithium aluminium tetrahydride; n-butyllithium; jones' reagent; diethylaluminium chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetone; 4: Diels-Alder reaction;
DOI:10.1016/S0040-4039(03)01176-6