(9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one

Base Information

• Chemical Name: (9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one
• CAS No.: 760210-89-7
• Molecular Formula: C₂₆H₂₈O₆
• Molecular Weight: 436.505

Synonyms:(9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one

Chemical Property of (9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one

Chemical Property:

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Technology Process of (9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one

There total 14 articles about (9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one 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:

(2S,4S)-2-phenyl-1,3-dioxane-4-carboxaldehyde (145958-02-7) → (9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one (760210-89-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 89 percent / Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 1.5 h / 20 °C

2.1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

3.1: K₂CO₃; methanol / 0.5 h / 0 °C

4.1: 1.42 g / H₂; quinoline / Lindlar's catalyst / methanol / 24 h / 20 °C

5.1: IBX; DMSO / 1 h / 20 °C

6.1: 1.10 g / PPh₃; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

7.1: 88 percent / n-Bu₃SnH; Pd(PPh₃)4 / benzene / 20 °C

8.1: 75 percent / DIBALH / CH₂Cl₂; toluene / 0.17 h / 0 °C

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

10.1: 355 mg / TBAF / tetrahydrofuran / 1.5 h / 0 °C

11.1: 79 percent / imidazole; DMAP / dimethylformamide / 0 - 20 °C

12.1: 2,5-dimethylhexa-2,4-diene; BH₃*SMe₂ / tetrahydrofuran; toluene / 0.5 h / 20 °C

12.2: aq. CH₂O / tetrahydrofuran

12.3: aq. KHF₂ / acetone; acetonitrile / 4 h / 20 °C

13.1: 28.5 mg / Pd(PPh₃)4; aq. Cs₂CO₃ / tetrahydrofuran / 20 h / Heating

With 1H-imidazole; quinoline; methanol; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,5-Dimethyl-2,4-hexadiene; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; caesium 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; 13.1: Suzuki coupling;

DOI:10.1021/ja047190o

Reference yield:

(4S,2'S,4'S)-4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-yn-1-ol (760210-81-9) → (9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one (760210-89-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1.42 g / H₂; quinoline / Lindlar's catalyst / methanol / 24 h / 20 °C

2.1: IBX; DMSO / 1 h / 20 °C

3.1: 1.10 g / PPh₃; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

4.1: 88 percent / n-Bu₃SnH; Pd(PPh₃)4 / benzene / 20 °C

5.1: 75 percent / DIBALH / CH₂Cl₂; toluene / 0.17 h / 0 °C

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

7.1: 355 mg / TBAF / tetrahydrofuran / 1.5 h / 0 °C

8.1: 79 percent / imidazole; DMAP / dimethylformamide / 0 - 20 °C

9.1: 2,5-dimethylhexa-2,4-diene; BH₃*SMe₂ / tetrahydrofuran; toluene / 0.5 h / 20 °C

9.2: aq. CH₂O / tetrahydrofuran

9.3: aq. KHF₂ / acetone; acetonitrile / 4 h / 20 °C

10.1: 28.5 mg / Pd(PPh₃)4; aq. Cs₂CO₃ / tetrahydrofuran / 20 h / Heating

With 1H-imidazole; quinoline; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,5-Dimethyl-2,4-hexadiene; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; caesium carbonate; 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; 10.1: Suzuki coupling;

DOI:10.1021/ja047190o

Reference yield:

(4S,2'S,4'S)-acetic acid 4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-ynyl ester (760210-80-8) → (9Z,11Z,13E)-(7S,8S)-7-(2-benzyloxyethyl)-4-hydroxy-8-methoxymethoxy-7,8-dihydro-6-oxabenzocyclododecen-5-one (760210-89-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: K₂CO₃; methanol / 0.5 h / 0 °C

2.1: 1.42 g / H₂; quinoline / Lindlar's catalyst / methanol / 24 h / 20 °C

3.1: IBX; DMSO / 1 h / 20 °C

4.1: 1.10 g / PPh₃; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

5.1: 88 percent / n-Bu₃SnH; Pd(PPh₃)4 / benzene / 20 °C

6.1: 75 percent / DIBALH / CH₂Cl₂; toluene / 0.17 h / 0 °C

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

8.1: 355 mg / TBAF / tetrahydrofuran / 1.5 h / 0 °C

9.1: 79 percent / imidazole; DMAP / dimethylformamide / 0 - 20 °C

10.1: 2,5-dimethylhexa-2,4-diene; BH₃*SMe₂ / tetrahydrofuran; toluene / 0.5 h / 20 °C

10.2: aq. CH₂O / tetrahydrofuran

10.3: aq. KHF₂ / acetone; acetonitrile / 4 h / 20 °C

11.1: 28.5 mg / Pd(PPh₃)4; aq. Cs₂CO₃ / tetrahydrofuran / 20 h / Heating

With 1H-imidazole; quinoline; methanol; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,5-Dimethyl-2,4-hexadiene; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; 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; 11.1: Suzuki coupling;

DOI:10.1021/ja047190o

upstream raw materials:

(2S,4S)-2-phenyl-1,3-dioxane-4-carboxaldehyde

(Z)-(4S,2'S,4'S)-4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-enal

(Z)-(4S,2'S,4'S)-4-methoxymethoxy-4-(2'-phenyl-[1,3]dioxan-4'-yl)but-2-en-1-ol

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

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