Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl ester
• CAS No.: 245509-18-6
• Molecular Formula: C₃₁H₄₀O₆
• Molecular Weight: 508.655
• Mol file: 245509-18-6.mol

Synonyms:Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl ester

Chemical Property of Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl ester

There total 4 articles about Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl 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: 52.0%

benzoyl chloride (98-88-4) + Acetic acid (1S,2R,3R,5R,1'S,2'R,5'R)-2-acetoxymethyl-5-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-2'-hydroxy-5'-methyl-bicyclopentyl-3'-en-3-yl ester (245509-17-5) → Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl ester (245509-18-6)

Guidance literature:

With pyridine; at 0 ℃; for 0.5h;

DOI:10.1021/jo9902190

Reference yield:

(5R,13Z)-5-acetoxy-10-oxo-4,10-secospata-2,13(15),17-trien-12-al (81575-01-1) → Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl ester (245509-18-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 31 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.17 h / 0 °C

2: 52 percent / pyridine / 0.25 h / 0 °C

3: 52 percent / pyridine / 0.5 h / 0 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; In methanol; 1: Reduction / 2: Acetylation / 3: Esterification;

DOI:10.1021/jo9902190

Reference yield:

dilkamural → Benzoic acid (1S,2R,5R,1'S,2'R,3'R,5'R)-3'-acetoxy-2'-acetoxymethyl-5'-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5-methyl-bicyclopentyl-3-en-2-yl ester (245509-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / Kieselgel 60 / CH₂Cl₂

2: 31 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.17 h / 0 °C

3: 52 percent / pyridine / 0.25 h / 0 °C

4: 52 percent / pyridine / 0.5 h / 0 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; Kieselgel 60; In methanol; dichloromethane; 1: Elimination / 2: Reduction / 3: Acetylation / 4: Esterification;

DOI:10.1021/jo9902190

upstream raw materials:

benzoyl chloride

Acetic acid (1S,2R,3R,5R,1'S,2'R,5'R)-2-acetoxymethyl-5-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-2'-hydroxy-5'-methyl-bicyclopentyl-3'-en-3-yl ester

(5R,13Z)-5-acetoxy-10-oxo-4,10-secospata-2,13⁽¹⁵⁾,17-trien-12-al

Acetic acid (1S,2R,3R,5R,1'S,2'R,5'R)-5-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-2'-hydroxy-2-hydroxymethyl-5'-methyl-bicyclopentyl-3'-en-3-yl ester