(4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate

Base Information

• Chemical Name: (4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate
• CAS No.: 1309369-05-8
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 1309369-05-8.mol

Synonyms:(4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate

Chemical Property of (4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate

There total 4 articles about (4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate 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: 90.7%

(3R,4S)-3-methoxy-2-methylhept-6-ene-2,4-diol (1309369-03-6) + benzoyl chloride (98-88-4) → (4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate (1309369-05-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2011.02.092

Reference yield:

(3R,4R)-3-(tert-butyldimethylsilyloxy)-4-methoxy-2,5-dimethylhexane-2,5-diol (1309369-00-3) → (4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate (1309369-05-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

2: sodium periodate / methanol; water / 13 h / 20 °C

3: cerium(III) chloride / tetrahydrofuran; diethyl ether; toluene / 12 h / -20 °C

4: triethylamine / dichloromethane / 0 - 20 °C

With sodium periodate; cerium(III) chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;

DOI:10.1016/j.tetlet.2011.02.092

Reference yield:

(3R,4R)-4-methoxy-2,5-dimethylhexane-2,3,5-triol (1309369-01-4) → (4S,5R)-6-hydroxy-5-methoxy-6-methylhept-1-en-4-yl benzoate (1309369-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium periodate / methanol; water / 13 h / 20 °C

2: cerium(III) chloride / tetrahydrofuran; diethyl ether; toluene / 12 h / -20 °C

3: triethylamine / dichloromethane / 0 - 20 °C

With sodium periodate; cerium(III) chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;

DOI:10.1016/j.tetlet.2011.02.092

upstream raw materials:

(3R,4R)-3-(tert-butyldimethylsilyloxy)-4-methoxy-2,5-dimethylhexane-2,5-diol

(3R,4R)-4-methoxy-2,5-dimethylhexane-2,3,5-triol

(S)-3-hydroxy-2-methoxy-3-methylbutanal

(3R,4S)-3-methoxy-2-methylhept-6-ene-2,4-diol

Downstream raw materials:

3-methoxy-2,2-dimethyl-3,4-dihydro-2H-pyran-4-yl benzoate