Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-4-ynyl ester

Base Information

• Chemical Name: Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-4-ynyl ester
• CAS No.: 105470-57-3
• Molecular Formula: C₃₁H₄₂O₇
• Molecular Weight: 526.67
• Mol file: 105470-57-3.mol

Synonyms:Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-4-ynyl ester

Chemical Property of Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-4-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-4-ynyl ester

There total 8 articles about Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-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:

[(4R,5S)-2,2-Dimethyl-5-((Z)-pent-2-enyl)-[1,3]dioxolan-4-yl]-methanol (105499-53-4) → Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-4-ynyl ester (105470-57-3)

Guidance literature:

Multi-step reaction with 5 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

With n-butyllithium; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; lithium diisopropyl amide; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4039(00)84105-2

Reference yield:

(2S,3S)-2,3-isopropylidenedioxyoctanal (88557-32-8) → Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-4-ynyl ester (105470-57-3)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / methanol

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

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

With n-butyllithium; boron trifluoride diethyl etherate; potassium carbonate; lithium diisopropyl amide; In methanol;

DOI:10.1016/S0040-4039(00)84105-2

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → Benzoic acid (6E,8E)-(1S,2R)-9-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(3-methoxycarbonyl-propyl)-nona-6,8-dien-4-ynyl ester (105470-57-3)

Guidance literature:

Multi-step reaction with 3 steps

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

With n-butyllithium; boron trifluoride diethyl etherate;

DOI:10.1016/S0040-4039(00)84105-2

upstream raw materials:

(4S,5S)-4-((1E,3E)-Hexa-1,3-dien-5-ynyl)-2,2-dimethyl-5-pentyl-[1,3]dioxolane

Benzoic acid (S)-4-methoxycarbonyl-1-(R)-oxiranyl-butyl ester

2-deoxy-D-ribose

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

Downstream raw materials:

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

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

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