(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

Base Information

• Chemical Name: (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
• CAS No.: 895579-29-0
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• Mol file: 895579-29-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 11 articles about (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 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: 75.0%

(2R,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid (895579-27-8) → (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 (895579-29-0)

Guidance literature:

(2R,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid; With pyridine; methanesulfonyl chloride; In dichloromethane; at 20 ℃; for 19h;

With hydrogenchloride; In dichloromethane;

DOI:10.1021/ja061970a

Reference yield:

ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate (895579-15-4) → (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 (895579-29-0)

Guidance literature:

Multi-step reaction with 10 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

9.1: 94 percent / H₂ / Pd/C / methanol; acetic acid / 2 h

10.1: pyridine; methanesulfonyl chloride / CH₂Cl₂ / 19 h / 20 °C

10.2: 75 percent / aq. HCl / CH₂Cl₂

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

DOI:10.1021/ja061970a

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-carbaldehyde (895579-06-3) → (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 (895579-29-0)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: 245 mg / potassium hydrogencarbonate; potassium fluoride; aq. hydrogen peroxide / dimethylformamide / 11 h / 20 °C

3.1: 94 percent / H₂ / Pd/C / methanol; acetic acid / 2 h

4.1: pyridine; methanesulfonyl chloride / CH₂Cl₂ / 19 h / 20 °C

4.2: 75 percent / aq. HCl / CH₂Cl₂

With pyridine; potassium fluoride; sodium chlorite; 2-methyl-but-2-ene; hydrogen; dihydrogen peroxide; potassium hydrogencarbonate; methanesulfonyl chloride; sodium phosphate; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ja061970a

upstream 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

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