Methyl barbascoate

Base Information

• Chemical Name: Methyl barbascoate
• CAS No.: 60132-72-1
• Molecular Weight: 358.43
• Mol file: 60132-72-1.mol

Synonyms:(2R)-2-(3-Furyl)-1,4,4aβ,5,6,6a,9,10,10aβ,10b-decahydro-6aα,10bα-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester;(2R)-2α-(3-Furyl)-1,4,4aβ,5,6,6a,9,10,10aβ,10b-decahydro-6aα,10bα-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester;(2R)-2α-(Furan-3-yl)-4-oxo-6aα,10bα-dimethyl-1,2,4aβ,5,6,6a,9,10,10aβ,10b-decahydro-4H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester;Barbascoic acid methyl;Methyl barbascoate

Chemical Property of Methyl barbascoate

Chemical Property:

• Melting Point: 152 °C
• Boiling Point: 490.7±45.0 °C(Predicted)
• Density: 1.181±0.06 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl barbascoate

There total 14 articles about Methyl barbascoate 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: 86.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 13-(3-furyl)-1,7-dimethyl-12-oxa-11-oxotricyclo[8.4.0.02,7]tetradec-5-en-6-yl trifluoromethanesulfonate (849825-37-2) → methyl 13-(3-furyl)-1,7-dimethyl-12-oxa-11-oxotricyclo[8.4.0.02,7]tetradec-5-ene-6-carboxylate (60132-72-1)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; tributyl-amine; palladium diacetate; In N,N-dimethyl-formamide; at 90 ℃; for 1.05h;

DOI:10.1021/jo0478499

Reference yield:

(4a'R,5'R,8a'R)-5',8a'-dimethyl-5'-(2-((triisopropylsilyl)oxy)ethyl)hexahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one (161006-56-0) → methyl 13-(3-furyl)-1,7-dimethyl-12-oxa-11-oxotricyclo[8.4.0.02,7]tetradec-5-ene-6-carboxylate (60132-72-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 87 percent / NaHMDS / tetrahydrofuran / 4 h / 65 °C

2.1: 97 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

3.1: 85 percent / SO₃-pyridine complex; DMSO; Et₃N / CH₂Cl₂ / 2 h / 0 °C

4.1: 20 percent / t-BuLi / tetrahydrofuran; pentane / 3 h / -78 °C

5.1: 91 percent / imidazole; DMAP / dimethylformamide / 15 h / 20 °C

6.1: BH₃ / tetrahydrofuran / 15 h / 20 °C

6.2: 32 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 22 h

7.1: pyridinium dichromate; AcONa / CH₂Cl₂ / 2 h / 20 °C

7.2: 23 mg / NaH / methanol / 12 h / 20 °C

8.1: 21 mg / TBAF / tetrahydrofuran / 12 h

9.1: 12 mg / NaOAc; pyridinium dichromate / CH₂Cl₂ / 6.5 h / 20 °C

10.1: 40 percent / PPTS / H₂O; acetone / Heating

11.1: 80 percent / NaHMDS / tetrahydrofuran / 1.3 h / -30 °C

12.1: 86 percent / n-Bu₃N; DPPF / Pd(OAc)2 / dimethylformamide / 1.05 h / 90 °C

With 1H-imidazole; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; dipyridinium dichromate; pyridine-SO₃ complex; tributyl-amine; borane; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium acetate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; pentane;

DOI:10.1021/jo0478499

Reference yield:

C17H26O3 (849824-95-9) → methyl 13-(3-furyl)-1,7-dimethyl-12-oxa-11-oxotricyclo[8.4.0.02,7]tetradec-5-ene-6-carboxylate (60132-72-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 20 percent / t-BuLi / tetrahydrofuran; pentane / 3 h / -78 °C

2.1: 91 percent / imidazole; DMAP / dimethylformamide / 15 h / 20 °C

3.1: BH₃ / tetrahydrofuran / 15 h / 20 °C

3.2: 32 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 22 h

4.1: pyridinium dichromate; AcONa / CH₂Cl₂ / 2 h / 20 °C

4.2: 23 mg / NaH / methanol / 12 h / 20 °C

5.1: 21 mg / TBAF / tetrahydrofuran / 12 h

6.1: 12 mg / NaOAc; pyridinium dichromate / CH₂Cl₂ / 6.5 h / 20 °C

7.1: 40 percent / PPTS / H₂O; acetone / Heating

8.1: 80 percent / NaHMDS / tetrahydrofuran / 1.3 h / -30 °C

9.1: 86 percent / n-Bu₃N; DPPF / Pd(OAc)2 / dimethylformamide / 1.05 h / 90 °C

With 1H-imidazole; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; dipyridinium dichromate; tributyl-amine; borane; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium acetate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; palladium diacetate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; pentane;

DOI:10.1021/jo0478499

upstream raw materials:

methanol

carbon monoxide

13-(3-furyl)-1,7-dimethyl-12-oxa-11-oxotricyclo[8.4.0.0^2,7]tetradec-5-en-6-yl trifluoromethanesulfonate

(4a'R,5'R,8a'R)-5',8a'-dimethyl-5'-(2-((triisopropylsilyl)oxy)ethyl)hexahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one