(2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide

Base Information

• Chemical Name: (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide
• CAS No.: 345319-69-9
• Molecular Formula: C₄₂H₅₁NO₅Si
• Molecular Weight: 677.956
• Mol file: 345319-69-9.mol

Synonyms:(2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide

Chemical Property of (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide

There total 26 articles about (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide 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: 70.0%

(2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-10-methyl-5-oxo-4-triisopropylsilanyloxy-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide (345319-68-8) → (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide (345319-69-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(01)00278-7

Reference yield:

((2S,3S)-3-(3-(benzyloxy)propyl)oxiran-2-yl)methanol (83458-92-8) → (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide (345319-69-9)

Guidance literature:

Multi-step reaction with 18 steps

1.1: NaAl(OMe)3H / tetrahydrofuran / 0 - 20 °C

2.1: TMSCl / methanol; tetrahydrofuran / 16 h / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / 1 h / 0 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: toluene / 8 h / -78 °C

6.1: imidazole / dimethylformamide / 16 h / 100 °C

7.1: 9-BBN / tetrahydrofuran / 0.5 h / 20 °C

7.2: NaBO₃ / 16 h / 20 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

9.1: tetrahydrofuran / 1 h / -78 - 20 °C

10.1: DDQ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

11.1: 73 percent / DEAD; PPh₃ / diethyl ether / 1 h / 0 - 20 °C

12.1: bis(tricyclohexylphosphine)benzylidine ruthenium(VI) Cl₂ / CH₂Cl₂ / 3 h / Heating

13.1: 80 percent / BBr₃ / CH₂Cl₂ / 0.5 h / -78 °C

14.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / 20 °C

15.1: DIPEA; DMAP / dimethylformamide / 1 h / 70 °C

16.1: TMSOTf / 1,2-dichloro-ethane / 2 h / 20 °C

17.1: NaH / various solvent(s) / 4.5 h / 60 °C

18.1: 70 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; trimethylsilyl trifluoromethanesulfonate; NaAl(OMe)3H; 4 A molecular sieve; tetrabutyl ammonium fluoride; boron tribromide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 4.1: Dess-Martin oxidation / 8.1: Dess-Martin oxidation / 11.1: Mitsunobu esterification;

DOI:10.1016/S0040-4039(01)00278-7

Reference yield:

(3S)-6-(Benzyloxy)hexane-1,3-diol (83458-93-9) → (2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide (345319-69-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: TMSCl / methanol; tetrahydrofuran / 16 h / 20 °C

2.1: DIBAL-H / CH₂Cl₂ / 1 h / 0 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: toluene / 8 h / -78 °C

5.1: imidazole / dimethylformamide / 16 h / 100 °C

6.1: 9-BBN / tetrahydrofuran / 0.5 h / 20 °C

6.2: NaBO₃ / 16 h / 20 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

8.1: tetrahydrofuran / 1 h / -78 - 20 °C

9.1: DDQ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

10.1: 73 percent / DEAD; PPh₃ / diethyl ether / 1 h / 0 - 20 °C

11.1: bis(tricyclohexylphosphine)benzylidine ruthenium(VI) Cl₂ / CH₂Cl₂ / 3 h / Heating

12.1: 80 percent / BBr₃ / CH₂Cl₂ / 0.5 h / -78 °C

13.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / 20 °C

14.1: DIPEA; DMAP / dimethylformamide / 1 h / 70 °C

15.1: TMSOTf / 1,2-dichloro-ethane / 2 h / 20 °C

16.1: NaH / various solvent(s) / 4.5 h / 60 °C

17.1: 70 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; boron tribromide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 3.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 10.1: Mitsunobu esterification;

DOI:10.1016/S0040-4039(01)00278-7

upstream raw materials:

(2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7R,9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-10-methyl-5-oxo-4-triisopropylsilanyloxy-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide

cis-2-penten-1-ol

cis-2-penten-1-one

((2S,3S)-3-(3-(benzyloxy)propyl)oxiran-2-yl)methanol

Downstream raw materials:

ent-salicylihalamide B

(+)-Salicylihalamide A