(3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone

Base Information

• Chemical Name: (3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone
• CAS No.: 150716-73-7
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 150716-73-7.mol

Synonyms:(3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone

Chemical Property of (3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone

There total 12 articles about (3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone 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: 93.0%

(1S,2R,3S)-3-<(tert-Butoxycarbonyl)amino>-3-(2-furyl)-1-(p-methoxyphenyl)-2-methyl-1-propanol (150823-44-2) → (3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone (150716-73-7)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; oxygen; ozone; In methanol; dichloromethane; 1.) -78 deg C, 2.) r.t., 1 h;

DOI:10.1021/jo00074a024

Reference yield:

<1-(p-Methoxyphenyl)propylidene>-p-tolylamine → (3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone (150716-73-7)

Guidance literature:

Multi-step reaction with 9 steps

2: 72 percent / 60 °C

3: 97 percent / NaBH₄ / methanol / Ambient temperature

4: 2 N H₂SO₄ / 1 h / 40 °C

5: NaOH / H₂O; 2-methyl-propan-2-ol

6: TFA / CH₂Cl₂ / 1 h / Ambient temperature

7: N-Selectride / tetrahydrofuran / Ambient temperature

8: NaOH / H₂O; 2-methyl-propan-2-ol

9: 93 percent / O₃/O₂, NaOH, 30percent H₂O₂ / CH₂Cl₂; methanol / 1.) -78 deg C, 2.) r.t., 1 h

With sodium hydroxide; sodium tetrahydroborate; sulfuric acid; dihydrogen peroxide; oxygen; sodium tri-sec-butylborohydride; ozone; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo00074a024

Reference yield:

2-(2-Furyl)-4-(p-methoxyphenyl)-3-methyl-4-(p-tolylamino)-1-aza-1,3-butadiene (150716-67-9) → (3S,4R,5S)-3-<(tert-Butoxycarbonyl)amino>-5-(p-methoxyphenyl)-4-methyltetrahydrofuranone (150716-73-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 72 percent / 60 °C

2: 97 percent / NaBH₄ / methanol / Ambient temperature

3: 2 N H₂SO₄ / 1 h / 40 °C

4: NaOH / H₂O; 2-methyl-propan-2-ol

5: TFA / CH₂Cl₂ / 1 h / Ambient temperature

6: N-Selectride / tetrahydrofuran / Ambient temperature

7: NaOH / H₂O; 2-methyl-propan-2-ol

8: 93 percent / O₃/O₂, NaOH, 30percent H₂O₂ / CH₂Cl₂; methanol / 1.) -78 deg C, 2.) r.t., 1 h

With sodium hydroxide; sodium tetrahydroborate; sulfuric acid; dihydrogen peroxide; oxygen; sodium tri-sec-butylborohydride; ozone; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo00074a024

upstream raw materials:

(1S,2R,3S)-3-<(tert-Butoxycarbonyl)amino>-3-(2-furyl)-1-(p-methoxyphenyl)-2-methyl-1-propanol

di-tert-butyl dicarbonate

2-(2-Furyl)-4-(p-methoxyphenyl)-3-methyl-4-(p-tolylamino)-1-aza-1,3-butadiene

(2R,3S)-3-Amino-3-(2-furyl)-1-(p-methoxyphenyl)-2-methyl-1-propanone