Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester

Base Information

• Chemical Name: Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester
• CAS No.: 373389-61-8
• Molecular Formula: C₃₇H₅₅NO₃
• Molecular Weight: 561.849
• Mol file: 373389-61-8.mol

Synonyms:Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester

Chemical Property of Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester

There total 15 articles about Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-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:

Methanesulfonic acid (4E,8E)-(R)-1-(1-hydroxy-1-methyl-ethyl)-4,8-dimethyl-11-((1S,4aR,6S,8aR)-5,5,8a-trimethyl-2-methylene-6-phenylcarbamoyloxy-decahydro-naphthalen-1-yl)-undeca-4,8-dienyl ester → Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester (373389-61-8)

Guidance literature:

With potassium carbonate; In methanol; dichloromethane; at 23 ℃; for 5h;

DOI:10.1021/ol016543a

Reference yield:

(2E,6E)-farnesyl acetate (4128-17-0) → Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester (373389-61-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 72 percent / MeSO₂NH₂; K₂OsO₄*2H₂O; K₃Fe(CN)6 / chiral monocinchona derivative C₇₀H₆₃N₅O₃; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 4 h / 0 °C

2.1: p-TsOH / 0.5 h / 23 °C

3.1: K₂CO₃ / methanol / 1 h / 23 °C

4.1: MeSO₂Cl; Et₃N / CH₂Cl₂ / 1.5 h / -42 - 0 °C

4.2: LiBr / tetrahydrofuran / 1 h / 0 °C

5.1: LDA; CuI / tetrahydrofuran / -110 - -30 °C

5.2: 92 percent / tetrahydrofuran / 1 h / -30 °C

6.1: LiAlH₄ / diethyl ether / 0.5 h / Heating

7.1: Ph₃P; imidazole; I₂ / CH₂Cl₂ / 0.5 h / 23 °C

8.1: 1.10 g / dimethylformamide / 24 h / 23 °C

9.1: BuLi / tetrahydrofuran; diethyl ether; hexane / 0.17 h / -78 °C

9.2: 75 percent / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C

10.1: Me₂AlCl₂ / CH₂Cl₂ / 0.25 h / -94 °C

10.2: TBAF / tetrahydrofuran / 15 h / 50 °C

10.3: 75 percent / KOH / methanol / 3 h / Heating

11.1: 75 percent / pyridine / 12 h / 23 °C

12.1: 90 percent / KOtBu / benzene; tetrahydrofuran / 2 h / Heating

13.1: aq. HOAc / 5 h / 55 °C

14.1: pyridine / CH₂Cl₂ / 12 h / 23 °C

15.1: 149 mg / K₂CO₃ / methanol; CH₂Cl₂ / 5 h / 23 °C

With pyridine; 1H-imidazole; potassium osmate(VI); copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; Me₂AlCl₂; potassium tert-butylate; iodine; potassium carbonate; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); lithium diisopropyl amide; chiral monocinchona derivative C₇₀H₆₃N₅O₃; potassium carbonate; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/ol016543a

Reference yield:

(R,2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienyl acetate (130790-62-4) → Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-10-((S)-3,3-dimethyl-oxiranyl)-4,8-dimethyl-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester (373389-61-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: p-TsOH / 0.5 h / 23 °C

2.1: K₂CO₃ / methanol / 1 h / 23 °C

3.1: MeSO₂Cl; Et₃N / CH₂Cl₂ / 1.5 h / -42 - 0 °C

3.2: LiBr / tetrahydrofuran / 1 h / 0 °C

4.1: LDA; CuI / tetrahydrofuran / -110 - -30 °C

4.2: 92 percent / tetrahydrofuran / 1 h / -30 °C

5.1: LiAlH₄ / diethyl ether / 0.5 h / Heating

6.1: Ph₃P; imidazole; I₂ / CH₂Cl₂ / 0.5 h / 23 °C

7.1: 1.10 g / dimethylformamide / 24 h / 23 °C

8.1: BuLi / tetrahydrofuran; diethyl ether; hexane / 0.17 h / -78 °C

8.2: 75 percent / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C

9.1: Me₂AlCl₂ / CH₂Cl₂ / 0.25 h / -94 °C

9.2: TBAF / tetrahydrofuran / 15 h / 50 °C

9.3: 75 percent / KOH / methanol / 3 h / Heating

10.1: 75 percent / pyridine / 12 h / 23 °C

11.1: 90 percent / KOtBu / benzene; tetrahydrofuran / 2 h / Heating

12.1: aq. HOAc / 5 h / 55 °C

13.1: pyridine / CH₂Cl₂ / 12 h / 23 °C

14.1: 149 mg / K₂CO₃ / methanol; CH₂Cl₂ / 5 h / 23 °C

With pyridine; 1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; Me₂AlCl₂; potassium tert-butylate; iodine; potassium carbonate; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ol016543a

upstream raw materials:

(2E,6E)-farnesyl acetate

(2E,6E)-3,7-dimethyl-9-((R)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)nona-2,6-dienyl acetate

(R,2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienyl acetate

(10R)-10,11-isopropylidenedioxy-10,11-dihydrofarnesyl bromide