(5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

Base Information

• Chemical Name: (5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one
• CAS No.: 682811-82-1
• Molecular Formula: C₃₀H₅₃NO₅Si₂
• Molecular Weight: 563.926
• Mol file: 682811-82-1.mol

Synonyms:(5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

Chemical Property of (5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

There total 5 articles about (5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one 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: 84.0%

benzyl chloride (100-44-7) + 5-[(tert-butyl-dimethyl-silanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-one (682811-90-1) → (5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one (682811-82-1)

Guidance literature:

With potassium hydride; In tetrahydrofuran; at 50 ℃; for 4h;

DOI:10.1021/jo035846a

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one (682811-82-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2: 92 percent / ceric ammonium nitrate / acetonitrile / 4 h / Heating

3: 84 percent / KH / tetrahydrofuran / 4 h / 50 °C

With 2,6-dimethylpyridine; ammonium cerium(IV) nitrate; potassium hydride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo035846a

Reference yield:

2-[(tert-butyldimethylsilanyloxy)methyl]-2-[(1R)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]-1-hydroxymethyl]-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester → (5S)-1-benzyl-5-[(1R)-1-(tert-butyldimethylsilanyloxy)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]methyl]-5-[(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one (682811-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / NiCl₂*6H₂O; NaBH₄ / methanol / 0 °C

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

3: 92 percent / ceric ammonium nitrate / acetonitrile / 4 h / Heating

4: 84 percent / KH / tetrahydrofuran / 4 h / 50 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; ammonium cerium(IV) nitrate; potassium hydride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo035846a

upstream raw materials:

benzyl chloride

5-[(tert-butyl-dimethyl-silanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-one

t-butyldimethylsiyl triflate

(2S)-2-[(tert-butyldimethylsilanyloxy)methyl]-2-[(1R)-1-[(4S)-2,2-dimethyl[1,3]dioxolan-4-yl]-1-hydroxymethyl]-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

1-benzyl-5-[1-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-one

(2R)-2-[(2S)-1-benzyl-2-[(tert-butyldimethylsilanyloxy)methyl]-5-oxopyrrolidin-2-yl]-2-(tert-butyldimethylsilanyloxy)acetaldehyde

(1S,4S,5R,6R)-2-benzyl-5,6-bis(tert-butyldimethylsilanyloxy)-1-[(tert-butyldimethylsilanyloxy)methyl]-2-azabicyclo[2.2.1]heptan-3-one