(3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 215370-54-0
• Molecular Formula: C₁₅H₂₈O₄Si
• Molecular Weight: 300.47
• Mol file: 215370-54-0.mol

Synonyms:

Chemical Property of (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

There total 7 articles about (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl 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: 83.0%

triethylsilyl chloride (994-30-9) + (3S,4R)-4-hydroxy-1-methoxycarbonyl-3-methyloxy-cyclohex-1-ene (215370-53-9) → (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester (215370-54-0)

Guidance literature:

With pyridine; for 0.5h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00284-5

Reference yield:

(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate (105539-78-4) → (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester (215370-54-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / n-Bu₃SnH, AIBN / benzene / 4 h / Heating

2: 89 percent / K₂CO₃ / 1 h / Ambient temperature

3: 1.) imidazole, 2.) pyridinium chlorochromate, 3 A molecular sieves, pyridine, 3.) POCl₃, pyridine

4: 0.8 g / NaBH₄ / methanol / 0.08 h / 0 °C

5: 88 percent / Ag₂O / CH₂Cl₂ / 48 h / Heating

6: 94 percent / n-Bu₄NF*3H₂O / tetrahydrofuran / 3 h / Ambient temperature

7: 83 percent / pyridine / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium carbonate; pyridinium chlorochromate; silver(l) oxide; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0957-4166(98)00284-5

Reference yield:

(1S,3R,4R)-1-methoxycarbonyl-cyclohexane-1,3,4-triol (215370-46-0) → (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester (215370-54-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) imidazole, 2.) pyridinium chlorochromate, 3 A molecular sieves, pyridine, 3.) POCl₃, pyridine

2: 0.8 g / NaBH₄ / methanol / 0.08 h / 0 °C

3: 88 percent / Ag₂O / CH₂Cl₂ / 48 h / Heating

4: 94 percent / n-Bu₄NF*3H₂O / tetrahydrofuran / 3 h / Ambient temperature

5: 83 percent / pyridine / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; 3 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium chlorochromate; silver(l) oxide; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0957-4166(98)00284-5

upstream raw materials:

triethylsilyl chloride

(3S,4R)-4-hydroxy-1-methoxycarbonyl-3-methyloxy-cyclohex-1-ene

(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate

(1S,3R,4R)-1-methoxycarbonyl-cyclohexane-1,3,4-triol

Downstream raw materials:

(1R,2S,3S,4R)-1,2-Dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexanecarboxylic acid methyl ester

(1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol

Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester