(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

Base Information

Chemical Name:(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde
CAS No.:1449483-41-3
Molecular Formula:C₂₃H₃₆O₃Si
Molecular Weight:388.623
Hs Code.:

Synonyms:

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Chemical Property of (2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

Chemical Property:

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Technology Process of (2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

There total 10 articles about (2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde 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:

: (4R,5R,6R,(E))-6-(benzyloxy)-9-bromo-5-(tert-butyldimethylsilyloxy)-4-methylnon-7-enal

: 1392307-55-9
(2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

: 1449483-41-3
(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

Guidance literature:: With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; Overall yield = 0.775 mg; Inert atmosphere;
DOI:10.1039/c3ob40692j

Reference yield:

: 1392307-53-7
((4R,5R,6R,(E))-4-(benzyloxy)-1-bromo-6,10-dimethylundeca-2,9-dien-5-yloxy)(tert-butyl)dimethylsilane

: 1392307-55-9
(2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

: 1449483-41-3
(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

2: periodic acid dihydrate / diethyl ether / 0.25 h

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 20 °C / Inert atmosphere

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; periodic acid dihydrate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1039/c3ob40692j

Reference yield:

: 106-72-9,77787-60-1,118333-87-2,116127-07-2
(R)-(-)-2,6-dimethyl-5-heptenal

: 1392307-55-9
(2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

: 1449483-41-3
(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 1.25 h / -78 - 0 °C / Inert atmosphere

1.2: 5.56 h / -78 - 0 °C / Inert atmosphere

1.3: 1 h / 0 °C / Inert atmosphere

2.1: 2,4,6-trimethyl-pyridine / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / water; tetrahydrofuran / 20 h / 0 - 20 °C

4.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

4.2: 20 h / 20 °C

5.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.25 h / -40 °C / Inert atmosphere

6.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 15 h / 0 °C / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

8.1: periodic acid dihydrate / diethyl ether / 0.25 h

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 20 °C / Inert atmosphere

With pyrrolidine; 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; periodic acid dihydrate; carbon tetrabromide; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;
DOI:10.1039/c3ob40692j