ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate

Base Information

Chemical Name:ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate
CAS No.:1392307-78-6
Molecular Formula:C₂₇H₄₀O₅Si
Molecular Weight:472.697
Hs Code.:

Synonyms:ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate

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Chemical Property of ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate

Chemical Property:

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Technology Process of ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate

There total 29 articles about ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate 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: 33.0%

: 1392307-57-1
(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanone

: 623-47-2
propynoic acid ethyl ester

: 1392307-78-6
ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate

Guidance literature:: propynoic acid ethyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanone; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;
DOI:10.1039/c3ob40692j

Reference yield:

: 42217-00-5
3,3,3-triethoxypropyne

: 1392307-57-1
(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanone

: 1392307-78-6
ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate

: 1392307-58-2
(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-methyl-1-(3,3,3-triethoxyprop-1-ynyl)-2-vinylcyclohexanol

Guidance literature:: 3,3,3-triethoxypropyne; With n-butyllithium; N-ethyl-N,N-diisopropylamine; In hexane; toluene; at -78 ℃; for 0.5h;

(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanone; In hexane; toluene; at -78 - 0 ℃;
DOI:10.1002/anie.201108223

Reference yield:

: 1392307-51-5
(4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate

: 1392307-78-6
ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate

Guidance literature:: Multi-step reaction with 8 steps

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

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

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

4.1: periodic acid dihydrate / diethyl ether / 0.25 h

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

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

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

7.2: 2 h / 20 °C

8.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

8.2: 2 h / -78 - 20 °C

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