(E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

• Chemical Name: (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS No.: 191274-20-1
• Molecular Formula: C₂₆H₄₂O₄
• Molecular Weight: 418.617
• Mol file: 191274-20-1.mol

Synonyms:

Chemical Property of (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

There total 3 articles about (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl 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:

1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0) + (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoyl chloride (276864-79-0) → (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (191274-20-1)

Guidance literature:

With pyridine; sodium hydride; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(00)00097-1

Reference yield:

5-(2-methylene-5,5,8a-trimethyl-(1R,4aR,8aR)-decahydronaphthalen-1-yl)-3-methylpent-2E-enoic acid (20257-75-4) → (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (191274-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2 / benzene / 2.5 h / 20 - 45 °C

2: 96.2 mg / NaH; pyridine / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With pyridine; oxalyl dichloride; sodium hydride; In dichloromethane; benzene; 1: Substitution / 2: Esterification;

DOI:10.1016/S0040-4020(00)00097-1

Reference yield:

methyl ent-labda-8(17),13-E-dien-15-oate, methyl copalate (10395-37-6,13902-79-9,16633-28-6,17110-88-2,30801-12-8,67010-58-6,110662-53-8) → (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (191274-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / NaOH / methanol / 1.5 h / Heating

2: (COCl)2 / benzene / 2.5 h / 20 - 45 °C

3: 96.2 mg / NaH; pyridine / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With pyridine; sodium hydroxide; oxalyl dichloride; sodium hydride; In methanol; dichloromethane; benzene; 1: Hydrolysis / 2: Substitution / 3: Esterification;

DOI:10.1016/S0040-4020(00)00097-1

upstream raw materials:

1,2-O-isopropylidene-D-glycerol

(E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoyl chloride

5-(2-methylene-5,5,8a-trimethyl-(1R,4aR,8aR)-decahydronaphthalen-1-yl)-3-methylpent-2E-enoic acid

methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate