(S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol

Base Information

Chemical Name:(S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol
CAS No.:815578-02-0
Molecular Formula:C₂₈H₃₉IO₄
Molecular Weight:566.52
Hs Code.:

Synonyms:(S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol

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Chemical Property of (S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol

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Technology Process of (S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol

There total 8 articles about (S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol 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%

: 810682-32-7
(S)-3-iodo-1-methoxymethoxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde

: 815577-90-3
1-(((1S,2R)-3-iodo-2-methyl-2-vinylcyclohex-3-enyloxy)methyl)benzene

: 815578-02-0
(S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol

Guidance literature:: 1-(((1S,2R)-3-iodo-2-methyl-2-vinylcyclohex-3-enyloxy)methyl)benzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

(S)-3-iodo-1-methoxymethoxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde; In tetrahydrofuran; at -78 ℃; for 0.25h;
DOI:10.1021/ol0481939

Reference yield:

: 619335-62-5
(2R,3S)-2-Benzyloxymethyl-3-hydroxy-2-methyl-cyclohexanone

: 815578-02-0
(S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₂ / Pd/C / methanol / 10 h

2.1: CH₂Cl₂ / 3 h

3.1: hydrazine; Et₃N / ethanol / 48 h / 130 °C

4.1: I₂; DBU / diethyl ether / 20 °C

5.1: 97 percent / DIBALH / CH₂Cl₂ / 24 h

6.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

7.1: 93 percent / Zn; Me₃Al; PdCl₂ / tetrahydrofuran / 14 h

8.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

8.2: 99 percent / tetrahydrofuran / 0.25 h / -78 °C

With n-butyllithium; hydrogen; iodine; trimethylaluminum; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium dichloride; hydrazine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; 6.1: Dess-Martin oxidation;
DOI:10.1021/ol0481939

Reference yield:

: 619335-75-0
(2R,3S)-3-hydroxy-2-hydroxymethyl-2-methylcyclohexanone

: 815578-02-0
(S)-((5S,6S)-5-benzyloxy-6-methyl-6-vinylcyclohex-1-enyl)((S)-3-iodo-1-(methoxymethoxy)-2,2,4-trimethylcyclohex-3-enyl)methanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: CH₂Cl₂ / 3 h

2.1: hydrazine; Et₃N / ethanol / 48 h / 130 °C

3.1: I₂; DBU / diethyl ether / 20 °C

4.1: 97 percent / DIBALH / CH₂Cl₂ / 24 h

5.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

6.1: 93 percent / Zn; Me₃Al; PdCl₂ / tetrahydrofuran / 14 h

7.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

7.2: 99 percent / tetrahydrofuran / 0.25 h / -78 °C

With n-butyllithium; iodine; trimethylaluminum; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium dichloride; hydrazine; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 5.1: Dess-Martin oxidation;
DOI:10.1021/ol0481939