(2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid
• CAS No.: 895579-07-4
• Molecular Formula: C₁₈H₂₃NO₆
• Molecular Weight: 349.384
• Mol file: 895579-07-4.mol

Synonyms:(2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid

Chemical Property of (2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid

There total 9 articles about (2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid 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:

(3S,3aS,6S,6aR)-3-Isopropenyl-4-(4-methoxy-benzyl)-1,1,6-trimethyl-5-oxo-tetrahydro-2-oxa-4-aza-1-sila-pentalene-3a-carboxylic acid (895579-26-7) → (2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid (895579-07-4)

Guidance literature:

With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 11h;

DOI:10.1021/ja061970a

Reference yield:

ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate (895579-15-4) → (2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid (895579-07-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (S,S)-[(salen)Al]O / cyclohexane; 2-methyl-propan-2-ol / 120 h / 23 °C

2.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 4 h / -78 - 0 °C

3.1: sodium borohydride / methanol / 6 h / 0 °C

4.1: Dess-Martin periodinane / pyridine / 1.5 h / 20 °C

5.1: tetrahydrofuran / 4 h / -78 °C

6.1: Red-Al(R) / toluene / 3 h / -78 - 0 °C

7.1: sodium phosphate; sodium chlorite; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.58 h / 20 °C

8.1: 245 mg / potassium hydrogencarbonate; potassium fluoride; aq. hydrogen peroxide / dimethylformamide / 11 h / 20 °C

With potassium fluoride; sodium chlorite; sodium tetrahydroborate; 2-methyl-but-2-ene; dihydrogen peroxide; potassium hydrogencarbonate; Dess-Martin periodane; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium phosphate; lithium hexamethyldisilazane; [((S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine(-2H))Al]2O; In tetrahydrofuran; pyridine; methanol; cyclohexane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/ja061970a

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (2S,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid (895579-07-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CH₂Cl₂ / 9.5 h / 50 °C

1.2: 62 percent / sodium triacetoxyborohydride / CH₂Cl₂ / 1 h / 0 °C

2.1: (S,S)-[(salen)Al]O / cyclohexane; 2-methyl-propan-2-ol / 120 h / 23 °C

3.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 4 h / -78 - 0 °C

4.1: sodium borohydride / methanol / 6 h / 0 °C

5.1: Dess-Martin periodinane / pyridine / 1.5 h / 20 °C

6.1: tetrahydrofuran / 4 h / -78 °C

7.1: Red-Al(R) / toluene / 3 h / -78 - 0 °C

8.1: sodium phosphate; sodium chlorite; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.58 h / 20 °C

9.1: 245 mg / potassium hydrogencarbonate; potassium fluoride; aq. hydrogen peroxide / dimethylformamide / 11 h / 20 °C

With potassium fluoride; sodium chlorite; sodium tetrahydroborate; 2-methyl-but-2-ene; dihydrogen peroxide; potassium hydrogencarbonate; Dess-Martin periodane; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium phosphate; lithium hexamethyldisilazane; [((S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine(-2H))Al]2O; In tetrahydrofuran; pyridine; methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/ja061970a

upstream raw materials:

(3S,3aS,6S,6aR)-3-Isopropenyl-4-(4-methoxy-benzyl)-1,1,6-trimethyl-5-oxo-tetrahydro-2-oxa-4-aza-1-sila-pentalene-3a-carboxylic acid

ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate

(3S,3aS,6S,6aR)-3-Isopropenyl-4-(4-methoxy-benzyl)-1,1,6-trimethyl-5-oxo-tetrahydro-2-oxa-4-aza-1-sila-pentalene-3a-carbaldehyde

(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile

Downstream raw materials:

(2R,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid

(3S,4S,7R,8R)-8-Hydroxy-3-isopropyl-5-(4-methoxy-benzyl)-7-methyl-2-oxa-5-aza-spiro[3.4]octane-1,6-dione

(3S,4S,7R,8S)-8-Hydroxy-3-isopropyl-5-(4-methoxy-benzyl)-7-methyl-2-oxa-5-aza-spiro[3.4]octane-1,6-dione

Trifluoro-methanesulfonic acid (1S,4R,7R,8R)-1-isopropyl-5-(4-methoxy-benzyl)-7-methyl-3,6-dioxo-2-oxa-5-aza-spiro[3.4]oct-8-yl ester