(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol

Base Information

Chemical Name:(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol
CAS No.:1449483-55-9
Molecular Formula:C₂₄H₃₆O₃Si
Molecular Weight:400.634
Hs Code.:

Synonyms:(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol

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Chemical Property of (1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol

Chemical Property:

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Technology Process of (1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol

There total 17 articles about (1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol 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: 88.0%

: 1449483-54-8
(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-1-((trimethylsilyl)ethynyl)-2-vinylcyclohexanol

: 1449483-55-9
(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol

Guidance literature:: (1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-1-((trimethylsilyl)ethynyl)-2-vinylcyclohexanol; With potassium carbonate; In methanol; at 20 ℃; for 1h;

With hydrogenchloride; In water;
DOI:10.1039/c3ob40692j

Reference yield:

: 1392307-50-4
(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

: 1449483-55-9
(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol

Guidance literature:: Multi-step reaction with 10 steps

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

1.2: 20 h / 20 °C

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

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

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

5.1: periodic acid dihydrate / diethyl ether / 0.25 h

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

7.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

8.2: 2 h / 20 °C

9.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

9.2: 0.58 h / -78 - 20 °C / Inert atmosphere

10.1: potassium carbonate / methanol / 1 h / 20 °C

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; periodic acid dihydrate; carbon tetrabromide; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1039/c3ob40692j

Reference yield:

: (S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one

: 1449483-55-9
(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexanol

Guidance literature:: Multi-step reaction with 11 steps

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

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

2.2: 20 h / 20 °C

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

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

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

6.1: periodic acid dihydrate / diethyl ether / 0.25 h

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

8.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

9.2: 2 h / 20 °C

10.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

10.2: 0.58 h / -78 - 20 °C / Inert atmosphere

11.1: potassium carbonate / methanol / 1 h / 20 °C

With pyrrolidine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; periodic acid dihydrate; carbon tetrabromide; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene;
DOI:10.1039/c3ob40692j