Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester
• CAS No.: 314280-77-8
• Molecular Formula: C₂₉H₃₆O₆S
• Molecular Weight: 512.667
• Mol file: 314280-77-8.mol

Synonyms:Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Chemical Property of Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

There total 16 articles about Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl 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:

Benzoic acid (1R,2R)-1-((1R,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester (314281-04-4) → Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester (314280-77-8)

Guidance literature:

Benzoic acid (1R,2R)-1-((1R,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester; With perchloric acid; In acetonitrile; at 55 ℃; for 2h;

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 5h; Further stages.;

DOI:10.1021/ja0030820

Reference yield:

Benzoic acid (1R,2R)-1-((1S,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester (314281-06-6) → Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester (314280-77-8)

Guidance literature:

Benzoic acid (1R,2R)-1-((1S,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester; With perchloric acid; In acetonitrile; at 60 ℃; for 0.25h;

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 6h; Further stages.;

DOI:10.1021/ja0030820

Reference yield:

(R)-2-((R)-2-Methyl-1-methylsulfanylmethoxy-allyl)-oxirane (251305-18-7) → Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester (314280-77-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA; (+)-4,4a,5,6,7,8-hexahydro-4a-Me-2(3H)-Nph dimethylhydrazone / tetrahydrofuran / 6 h / -78 - 65 °C

1.2: tetrahydrofuran / 3.5 h

2.1: 76 percent / DMAP / CH₂Cl₂ / 23 h / 20 °C

3.1: 53 percent / NaOAc; AcOH / benzene / 16 h / 65 °C

4.1: 80 percent / aq. perchloric acid / acetonitrile / 0.25 h / 60 °C

5.1: 78 percent / pyridinium dichromate / CH₂Cl₂ / 5 h / 20 °C

With dmap; dipyridinium dichromate; perchloric acid; (+)-4,4a,5,6,7,8-hexahydro-4a-Me-2(3H)-Nph dimethylhydrazone; sodium acetate; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile; benzene; 1.1: Stork metalloenamine alkylation;

DOI:10.1021/ja034842k

upstream raw materials:

Benzoic acid (1R,2R)-1-[(1R,3aR,9aS,9bS)-7-(dimethyl-hydrazono)-1-methoxy-9a,9b-dimethyl-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Benzoic acid (1R,2R)-1-[(1S,3aR,9aS,9bS)-7-(dimethyl-hydrazono)-1-methoxy-9a,9b-dimethyl-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Benzoic acid (1R,2R)-1-((1R,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Benzoic acid (1R,2R)-1-((1S,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Downstream raw materials:

C₄₅H₅₂N₂O₇Se

Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-hydroxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester