Benzoic acid (S)-2-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester

Base Information

• Chemical Name: Benzoic acid (S)-2-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester
• CAS No.: 112497-08-2
• Molecular Formula: C₃₁H₄₆O₁₀S
• Molecular Weight: 610.766

Synonyms:

Chemical Property of Benzoic acid (S)-2-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (S)-2-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester

There total 9 articles about Benzoic acid (S)-2-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl 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:

(Z)-1-Bromo-6-methoxymethoxy-3-methyl-hex-2-ene (112496-98-7) → Benzoic acid (S)-2-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester (112497-08-2,112573-33-8)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran / 0 deg C to room temp., via the dianion

2: TEA, DMAP, HMPA / -20 deg C to room temp.

3: CuI / tetrahydrofuran / -45 °C

4: 53 percent / KMO₄, CO₂ / acetone; H₂O / -25 °C

5: LAH / tetrahydrofuran / 0 °C

6: pyridine / 0 °C

7: pyridine / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium permanganate; copper(l) iodide; lithium aluminium tetrahydride; carbon dioxide; TEA; In tetrahydrofuran; pyridine; water; acetone;

DOI:10.1016/S0040-4039(01)80974-6

Reference yield:

(Z)-6-Methoxymethoxy-3-methyl-hex-2-en-1-ol → Benzoic acid (S)-2-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester (112497-08-2,112573-33-8)

Guidance literature:

Multi-step reaction with 8 steps

1: PPh₃, CBr₄ / CH₂Cl₂ / -78 deg C to room temp.

2: tetrahydrofuran / 0 deg C to room temp., via the dianion

3: TEA, DMAP, HMPA / -20 deg C to room temp.

4: CuI / tetrahydrofuran / -45 °C

5: 53 percent / KMO₄, CO₂ / acetone; H₂O / -25 °C

6: LAH / tetrahydrofuran / 0 °C

7: pyridine / 0 °C

8: pyridine / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium permanganate; copper(l) iodide; lithium aluminium tetrahydride; carbon tetrabromide; carbon dioxide; TEA; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(01)80974-6

Reference yield:

(2Z,6Z)-10-Methoxymethoxy-3,7-dimethyl-deca-2,6-dienoic acid methyl ester (112496-99-8) → Benzoic acid (S)-2-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyloxy)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester (112497-08-2,112573-33-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 53 percent / KMO₄, CO₂ / acetone; H₂O / -25 °C

2: LAH / tetrahydrofuran / 0 °C

3: pyridine / 0 °C

4: pyridine / 0 °C

With potassium permanganate; lithium aluminium tetrahydride; carbon dioxide; In tetrahydrofuran; pyridine; water; acetone;

DOI:10.1016/S0040-4039(01)80974-6

upstream raw materials:

(7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid (S)-2-hydroxy-2-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester

benzoyl chloride

(Z)-1-Bromo-6-methoxymethoxy-3-methyl-hex-2-ene

(S)-1-[(2R,5S)-5-((R)-1-Hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethane-1,2-diol

Downstream raw materials:

(S)-Acetoxy-phenyl-acetic acid (S)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester

(S)-Acetoxy-phenyl-acetic acid (R)-1-[(2S,5R)-5-((S)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester

((S)-4-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-pentyl)-triphenyl-phosphonium; iodide

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