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

Base Information

• Chemical Name: (2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile
• CAS No.: 895579-04-1
• Molecular Formula: C₂₀H₂₆N₂O₃Si
• Molecular Weight: 370.524
• Mol file: 895579-04-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile 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:

(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile (895579-25-6) → (2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile (895579-04-1)

Guidance literature:

With Dess-Martin periodane; In pyridine; at 20 ℃; for 1.5h;

DOI:10.1021/ja061970a

Reference yield:

(E)-3-(allyldimethylsilyl)acrylaldehyde (895579-14-3) → (2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile (895579-04-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; sodium chlorite / 2-methyl-propan-2-ol / 0.5 h / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

2.2: 15.3 g / 1,1-carbonyldiimidazole / tetrahydrofuran; hexane / 0.83 h / -5 °C

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

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

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

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

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

With sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; Dess-Martin periodane; lithium hexamethyldisilazane; [((S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine(-2H))Al]2O; In tetrahydrofuran; pyridine; methanol; hexane; cyclohexane; tert-butyl alcohol;

DOI:10.1021/ja061970a

Reference yield:

3-(allyldimethylsilyl)prop-2-yn-1-ol (895579-11-0) → (2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile (895579-04-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Red-Al(R) / diethyl ether; toluene / 1 h / 0 - 20 °C

2.1: dimethylsulfoxide; triethylamine; SO₃*pyridine / CH₂Cl₂ / 5.5 h / 0 - 20 °C

3.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; sodium chlorite / 2-methyl-propan-2-ol / 0.5 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

4.2: 15.3 g / 1,1-carbonyldiimidazole / tetrahydrofuran; hexane / 0.83 h / -5 °C

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

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

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

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

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

With sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; pyridine-SO₃ complex; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; [((S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine(-2H))Al]2O; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; tert-butyl alcohol;

DOI:10.1021/ja061970a

upstream raw materials:

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

(E)-3-(allyldimethylsilyl)acrylaldehyde

3-(allyldimethylsilyl)prop-2-yn-1-ol

(E)-3-(allyldimethylsilyl)prop-2-en-1-ol

Downstream raw materials:

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

(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

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