(Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester

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Chemical Name:(Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester
CAS No.:760210-75-1
Molecular Formula:C₃₂H₄₁BrO₆Si
Molecular Weight:629.663
Hs Code.:

Synonyms:(Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester

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Chemical Property of (Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester

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Technology Process of (Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester

There total 12 articles about (Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester 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: 79.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 760210-88-6
(Z,Z)-(3S,4S)-2-ethynyl-6-hydroxy benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester

: 760210-75-1
(Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1021/ja047190o

Reference yield:

: 145958-02-7
(2S,4S)-2-phenyl-1,3-dioxane-4-carboxaldehyde

: 760210-75-1
(Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 1.5 h / 20 °C

2: i-Pr₂NEt / CH₂Cl₂ / 20 °C

3: K₂CO₃; methanol / 0.5 h / 0 °C

4: 1.42 g / H₂; quinoline / Lindlar's catalyst / methanol / 24 h / 20 °C

5: IBX; DMSO / 1 h / 20 °C

6: 1.10 g / PPh₃; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

7: 88 percent / n-Bu₃SnH; Pd(PPh₃)4 / benzene / 20 °C

8: 75 percent / DIBALH / CH₂Cl₂; toluene / 0.17 h / 0 °C

9: NaHMDS / tetrahydrofuran / 5 h / -20 - 0 °C

10: 355 mg / TBAF / tetrahydrofuran / 1.5 h / 0 °C

11: 79 percent / imidazole; DMAP / dimethylformamide / 0 - 20 °C

With 1H-imidazole; quinoline; methanol; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja047190o

Reference yield:

: 760210-81-9
(4S,2'S,4'S)-4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-yn-1-ol

: 760210-75-1
(Z,Z)-(3S,4S)-2-(tert-butyldimethylsilanyloxy)-6-ethynyl benzoic acid 3-(1-benzyloxy-8-bromo-4-methoxymethoxy-octa-5,7-dienyl) ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.42 g / H₂; quinoline / Lindlar's catalyst / methanol / 24 h / 20 °C

2: IBX; DMSO / 1 h / 20 °C

3: 1.10 g / PPh₃; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

4: 88 percent / n-Bu₃SnH; Pd(PPh₃)4 / benzene / 20 °C

5: 75 percent / DIBALH / CH₂Cl₂; toluene / 0.17 h / 0 °C

6: NaHMDS / tetrahydrofuran / 5 h / -20 - 0 °C

7: 355 mg / TBAF / tetrahydrofuran / 1.5 h / 0 °C

8: 79 percent / imidazole; DMAP / dimethylformamide / 0 - 20 °C

With 1H-imidazole; quinoline; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja047190o