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

Base Information

• Chemical Name: 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
• CAS No.: 314281-00-0
• Molecular Formula: C₃₂H₄₆N₂O₅S
• Molecular Weight: 570.794
• Mol file: 314281-00-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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:

benzoyl chloride (98-88-4) + (2R,3R)-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-yl]-4-methyl-3-methylsulfanylmethoxy-pent-4-en-2-ol → 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 (314281-00-0)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1021/ja0030820

Reference yield:

(R)-2,2-Dimethyl-4-((R)-2-methyl-1-methylsulfanylmethoxy-allyl)-[1,3]dioxolane (314280-90-5) → 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 (314281-00-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 percent / TsOH / methanol; H₂O / 2 h / 65 °C

2.1: 75 percent / Et₃N / CH₂Cl₂ / 7 h / 0 °C

3.1: 67 percent / K₂CO₃ / methanol / 2 h / 0 °C

4.1: LDA; host hydrazone / tetrahydrofuran / 5 h / 65 °C

4.2: 524 mg / tetrahydrofuran / 3.5 h / 20 °C

5.1: 387 mg / DMAP / CH₂Cl₂ / 23 h / 20 °C

With dmap; host hydrazone; potassium carbonate; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 4.2: Stork metalloenamine alkylation;

DOI:10.1021/ja0030820

Reference yield:

Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester (314280-92-7) → 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 (314281-00-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 67 percent / K₂CO₃ / methanol / 2 h / 0 °C

2.1: LDA; host hydrazone / tetrahydrofuran / 5 h / 65 °C

2.2: 524 mg / tetrahydrofuran / 3.5 h / 20 °C

3.1: 387 mg / DMAP / CH₂Cl₂ / 23 h / 20 °C

With dmap; host hydrazone; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 2.2: Stork metalloenamine alkylation;

DOI:10.1021/ja0030820

upstream raw materials:

benzoyl chloride

(2R,3R)-4-Methyl-3-methylsulfanylmethoxy-pent-4-ene-1,2-diol

(R)-2,2-Dimethyl-4-((R)-2-methyl-1-methylsulfanylmethoxy-allyl)-[1,3]dioxolane

Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester

Downstream raw materials:

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

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

C₄₅H₅₂N₂O₇Se

Benzoic acid (2R,3R,5S,8S,13R,14S)-3-isopropenyl-8,14-dimethyl-15-oxo-1,2,3,6,7,8,11,12,13,14,15,17-dodecahydro-5H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester