Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester

Base Information

Chemical Name:Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester
CAS No.:273944-73-3
Molecular Formula:C₅₉H₁₀₆O₁₀Si₃
Molecular Weight:1059.74
Hs Code.:

Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester

Synonyms:Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester

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Chemical Property of Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester

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Technology Process of Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester

There total 16 articles about Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl 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:

: 273944-71-1
(3S,4R,5R,6R,7R,8R)-8-benzoyloxy-6-diethylisopropylsilyloxy-4-hydroxy-3-methoxy-5,7-dimethylnon-1-yne

: 273944-72-2
(2Z,4E,6R,7R,8S,9S,10R,12E)-methyl 7,9-ditriethylsilyloxy-8-ethyl-13-iodo-2-methoxy-4,6,10,12-tetramethyltrideca-2,4,12-trienoate

: 273944-73-3
Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester

Guidance literature:: (3S,4R,5R,6R,7R,8R)-8-benzoyloxy-6-diethylisopropylsilyloxy-4-hydroxy-3-methoxy-5,7-dimethylnon-1-yne; With tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; at 20 ℃; for 0.166667h;

(2Z,4E,6R,7R,8S,9S,10R,12E)-methyl 7,9-ditriethylsilyloxy-8-ethyl-13-iodo-2-methoxy-4,6,10,12-tetramethyltrideca-2,4,12-trienoate; With 1-methyl-pyrrolidin-2-one; copper(I) thiophene-2-carboxylate; at 20 ℃; for 1h;
DOI:10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7

Reference yield:

: 107149-56-4
chlorodiethylisopropylsilane

: 273944-73-3
Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: imidazole / dimethylformamide / 16 h / 20 °C

2.1: H₂ / Pd(OH)2 / 3 h / 20 °C

3.1: DMSO; (COCl)2; NEt₃ / CH₂Cl₂ / 0.5 h / -78 - 0 °C

4.1: (cHex)2BCl; NEt₃ / diethyl ether / 3 h / 0 °C

4.2: diethyl ether / 16 h / -78 - -20 °C / pH 7

4.3: H₂O₂ / methanol / 1 h / 0 °C / pH 7

5.1: NaBH₄ / methanol / 0.5 h / 20 °C

6.1: K₂CO₃; MeOH / 0.5 h / 20 °C

7.1: Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.17 h / 20 °C

8.1: K₂CO₃ / methanol / 16 h / 20 °C

9.1: Bu₃SnH / [PdCl₂(PPh₃)2] / CH₂Cl₂ / 0.17 h / 20 °C

9.2: copper(I) thiophene-2-carboxylate; NMP / 1 h / 20 °C

With 1H-imidazole; lead(IV) acetate; methanol; sodium tetrahydroborate; oxalyl dichloride; dicyclohexylboron chloride; hydrogen; tri-n-butyl-tin hydride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrogenolysis / 3.1: Swern oxidation / 4.1: Substitution / 4.2: Addition / 4.3: Oxidation / 5.1: Reduction / 6.1: Saponification / 7.1: Oxidation / 8.1: Ohiga-Bestmann alkynation / 9.1: Addition / 9.2: Stille coupling reaction;
DOI:10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 273944-73-3
Benzoic acid (7E,9E,17E,19Z)-(1R,2R,3R,4R,5R,6S,12R,13S,14S,15R,16R)-3-(diethyl-isopropyl-silanyloxy)-14-ethyl-5-hydroxy-6,20-dimethoxy-20-methoxycarbonyl-1,2,4,10,12,16,18-heptamethyl-13,15-bis-triethylsilanyloxy-icosa-7,9,17,19-tetraenyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 - 0 °C

2.1: Bu₃SnH / [PdCl₂(PPh₃)2] / CH₂Cl₂ / 0.17 h / 20 °C

2.2: copper(I) thiophene-2-carboxylate; NMP / 1 h / 20 °C

With 2,6-dimethylpyridine; tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; 1.1: Etherification / 2.1: Addition / 2.2: Stille coupling reaction;
DOI:10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7