(2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol

Base Information

Chemical Name:(2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol
CAS No.:297153-50-5
Molecular Formula:C₂₅H₃₈O₂Si
Molecular Weight:398.661
Hs Code.:

Synonyms:(2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol

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Chemical Property of (2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol

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Technology Process of (2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol

There total 1 articles about (2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol 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: 77.0%

: 297153-49-2
(1'S,2'R,2S,3R,4E)-2'-(N-benzyl-N-mesitylenesulfonyl)amino-1'-phenyl-1'-propyl 3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenoate

: 187324-64-7
(1S,2R)-2-[N-benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol

: 297153-50-5
(2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 90 ℃; for 9h;
DOI:10.1021/jo000453m

Reference yield:

: 297153-50-5
(2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol

: (2E,8E,12E)-(10R,11R)-11-Hydroxy-2,10,12-trimethyl-15-naphthalen-2-yl-pentadeca-2,8,12-trien-6-ynoic acid ((S)-1-hydroxymethyl-2-phenyl-ethyl)-amide

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

2: 75 percent / CrCl₂ / tetrahydrofuran / 3 h / 0 °C

3: 97 percent / tert-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

4: (Ph₃)2PdCl₂; CuI; i-Pr₂NH / ethyl acetate / 0 - 20 °C

With chromium dichloride; copper(l) iodide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; tert-butyl-ammonium fluoride; (Ph₃)2PdCl₂; diisopropylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Oxidation / 2: Condensation / 3: Hydrolysis / 4: Condensation;
DOI:10.1021/jo000453m

Reference yield:

: 297153-50-5
(2R,3R,4E)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-7-(2''-naphthyl)-4-heptenol

: (2E,8E,10R,11R,12E)-N,N-dibenzyl 11-hydroxy-15-(2'-naphthyl)-2,10,12-trimethyl-2,8,12-pentadecatrien-6-ynamide

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

2: 75 percent / CrCl₂ / tetrahydrofuran / 3 h / 0 °C

3: 97 percent / tert-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

4: (Ph₃)2PdCl₂; CuI; i-Pr₂NH / ethyl acetate / 0 - 20 °C

With chromium dichloride; copper(l) iodide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; tert-butyl-ammonium fluoride; (Ph₃)2PdCl₂; diisopropylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Oxidation / 2: Condensation / 3: Hydrolysis / 4: Condensation;
DOI:10.1021/jo000453m