(1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate

Base Information

Chemical Name:(1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate
CAS No.:307492-68-8
Molecular Formula:C₃₅H₄₄O₅Si
Molecular Weight:572.817
Hs Code.:

Synonyms:(1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate

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Chemical Property of (1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate

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Technology Process of (1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate

There total 15 articles about (1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate 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: 95.0%

: 1392823-75-4
(1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-2-ene-1,5-diyl diacetate

: 307492-68-8
(1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; at 20 ℃; for 12h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo301210f

Reference yield: 87.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 307492-67-7
Acetic acid (E)-(1S,2R,3S)-3-acetoxy-1-((S)-2-hydroxy-1-methyl-ethyl)-2-methyl-5-phenyl-pent-4-enyl ester

: 307492-68-8
(1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 17h;
DOI:10.1016/S0040-4039(00)02002-5

Reference yield:

: 14371-10-9
(E)-3-phenylpropenal

: 307492-68-8
(1R,4R,5R,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diyl diacetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: Sn(OTf)2; triethylamine / CH₂Cl₂ / 2 h / -78 °C

1.2: 86 percent / CH₂Cl₂ / 1 h / -78 °C

2.1: 96 percent / Me₄NHB(OAc)3; AcOH / acetonitrile / 21 h / -40 - -20 °C

3.1: 84 percent / pyridine; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 81 percent / 2,3-dichloro-4,5-dicyanoquinone / CH₂Cl₂; H₂O / 1 h / 20 °C / pH 7

5.1: 87 percent / imidazole / dimethylformamide / 17 h / 20 °C

With pyridine; 1H-imidazole; dmap; tin(II) trifluoromethanesulfonate; 2,3-dichloro-4,5-dicyanoquinone; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)02002-5