Benzoic acid (2E,6E,8E)-(1S,10R,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester

Base Information

Chemical Name:Benzoic acid (2E,6E,8E)-(1S,10R,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester
CAS No.:105448-71-3
Molecular Formula:C₂₈H₃₆O₆
Molecular Weight:468.59
Hs Code.:

Synonyms:Benzoic acid (2E,6E,8E)-(1S,10R,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Benzoic acid (2E,6E,8E)-(1S,10R,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester

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Technology Process of Benzoic acid (2E,6E,8E)-(1S,10R,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester

There total 20 articles about Benzoic acid (2E,6E,8E)-(1S,10R,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl 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: 84.0%

: 105448-75-7,105499-55-6
Benzoic acid (2E,6E,8E)-(S)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-1-(3-methoxycarbonyl-propyl)-nona-2,6,8-trien-4-ynyl ester

: 105448-71-3,105499-56-7
Benzoic acid (2E,6E,8E)-(1S,10S,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester

Guidance literature:: With acetic acid; at 55 ℃;
DOI:10.1016/S0040-4039(00)84105-2

Reference yield: 73.0%

: 103001-18-9
Benzoic acid (2E,6E,8E)-(1S,10R,11S)-10,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester

: 105448-71-3
Benzoic acid (2E,6E,8E)-(1S,10R,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃;
DOI:10.1016/S0040-4039(00)84105-2

Reference yield:

: 105499-53-4
[(4R,5S)-2,2-Dimethyl-5-((Z)-pent-2-enyl)-[1,3]dioxolan-4-yl]-methanol

: 105448-71-3,105499-56-7
Benzoic acid (2E,6E,8E)-(1S,10S,11S)-10,11-dihydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,6,8-trien-4-ynyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) H₂ / 1.) Pd/C / 1.) EtOAc, 2.) Swern oxidation

2: K₂CO₃ / methanol

4: 1.) n-BuLi, 2.) LDA / 2.) 0 grad C, THF

5: 1.) n-BuLi, BF_3.OEt₂ / 2.) -78 grad C, THF

6: 63 percent / MSCl, Et₃N, DBU / tetrahydrofuran

7: 84 percent / 80percent aqueous HOAc / 55 °C

With n-butyllithium; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4039(00)84105-2