Carbamic acid, [(1S)-1-formyl-2-[4-methoxy-3-methyl-5-(2-propenyloxy)phenyl]ethyl]-, 2-propenyl ester

Base Information

• Chemical Name: Carbamic acid, [(1S)-1-formyl-2-[4-methoxy-3-methyl-5-(2-propenyloxy)phenyl]ethyl]-, 2-propenyl ester
• CAS No.: 686776-21-6
• Molecular Formula: C18H23NO5
• Molecular Weight: 333.384
• Mol file: 686776-21-6.mol

Synonyms:

Chemical Property of Carbamic acid, [(1S)-1-formyl-2-[4-methoxy-3-methyl-5-(2-propenyloxy)phenyl]ethyl]-, 2-propenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [(1S)-1-formyl-2-[4-methoxy-3-methyl-5-(2-propenyloxy)phenyl]ethyl]-, 2-propenyl ester

There total 12 articles about Carbamic acid, [(1S)-1-formyl-2-[4-methoxy-3-methyl-5-(2-propenyloxy)phenyl]ethyl]-, 2-propenyl 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: 92.0%

[(S)-2-(3-Allyloxy-4-methoxy-5-methyl-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid allyl ester (686776-29-4) → [(S)-2-(3-Allyloxy-4-methoxy-5-methyl-phenyl)-1-formyl-ethyl]-carbamic acid allyl ester (686776-21-6)

Guidance literature:

DOI:10.1055/s-2004-817763

Reference yield:

3-methylbenzene-1,2-diol (488-17-5) → [(S)-2-(3-Allyloxy-4-methoxy-5-methyl-phenyl)-1-formyl-ethyl]-carbamic acid allyl ester (686776-21-6)

Guidance literature:

Multi-step reaction with 12 steps

1: triethylamine / CH₂Cl₂ / 4 h / -70 °C

2: 23.5 g / K₂CO₃ / acetone / 5 h / 50 °C

3: 85 percent / TiCl₄ / CH₂Cl₂ / 20 °C

4: 99 percent / NaBH₄ / tetrahydrofuran; methanol; H₂O / 1 h / 0 °C

5: 95 percent / PBr₃ / CH₂Cl₂; toluene / 20 °C

6: O-⁽⁹⁾-allyl-N-(9'-anthracenylmethyl)cinchonidium bromide; CsOH*H₂O / CH₂Cl₂ / 30 h / -78 °C

7: AcOH / tetrahydrofuran; H₂O / 2 h / 20 °C

8: LiBH₄ / diethyl ether; methanol / 20 °C

9: NaOH / ethanol; H₂O / 8 h / 80 °C

10: NaHCO₃ / H₂O; CH₂Cl₂ / 1 h / 20 °C

11: K₂CO₃ / acetone / 4 h / Heating

12: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 1.17 h / -78 - 0 °C

With cesium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium borohydride; oxalyl dichloride; phosphorus tribromide; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; 12: Swern oxidation;

DOI:10.1021/jo050408k

Reference yield:

toluene-4-sulfonic acid 2-hydroxy-3-methyl-phenyl ester (244126-22-5) → [(S)-2-(3-Allyloxy-4-methoxy-5-methyl-phenyl)-1-formyl-ethyl]-carbamic acid allyl ester (686776-21-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 23.5 g / K₂CO₃ / acetone / 5 h / 50 °C

2: 85 percent / TiCl₄ / CH₂Cl₂ / 20 °C

3: 99 percent / NaBH₄ / tetrahydrofuran; methanol; H₂O / 1 h / 0 °C

4: 95 percent / PBr₃ / CH₂Cl₂; toluene / 20 °C

5: O-⁽⁹⁾-allyl-N-(9'-anthracenylmethyl)cinchonidium bromide; CsOH*H₂O / CH₂Cl₂ / 30 h / -78 °C

6: AcOH / tetrahydrofuran; H₂O / 2 h / 20 °C

7: LiBH₄ / diethyl ether; methanol / 20 °C

8: NaOH / ethanol; H₂O / 8 h / 80 °C

9: NaHCO₃ / H₂O; CH₂Cl₂ / 1 h / 20 °C

10: K₂CO₃ / acetone / 4 h / Heating

11: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 1.17 h / -78 - 0 °C

With cesium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium borohydride; oxalyl dichloride; phosphorus tribromide; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; 11: Swern oxidation;

DOI:10.1021/jo050408k

upstream raw materials:

[(S)-2-(3-Allyloxy-4-methoxy-5-methyl-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid allyl ester

3-methylbenzene-1,2-diol

toluene-4-sulfonic acid 2-hydroxy-3-methyl-phenyl ester

toluene-4-sulfonic acid 2-methoxy-3-methyl-phenyl ester

Downstream raw materials:

[(1S,2R)-2-((5R,7R,10R)-11-Allyloxy-7-hydroxymethyl-2,2,12-trimethyl-4,5,7,10-tetrahydro-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-6-yl)-1-(3-allyloxy-4-methoxy-5-methyl-benzyl)-2-cyano-ethyl]-carbamic acid allyl ester

C₆₆H₇₃Cl₃N₄O₁₆S