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

Base Information

• Chemical Name: (2R)-2-[(2S)-1-benzyl-2-[(tert-butyldimethylsilanyloxy)methyl]-5-oxopyrrolidin-2-yl]-2-(tert-butyldimethylsilanyloxy)acetaldehyde
• CAS No.: 682811-72-9
• Molecular Formula: C₂₆H₄₅NO₄Si₂
• Molecular Weight: 491.819
• Mol file: 682811-72-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2R)-2-[(2S)-1-benzyl-2-[(tert-butyldimethylsilanyloxy)methyl]-5-oxopyrrolidin-2-yl]-2-(tert-butyldimethylsilanyloxy)acetaldehyde 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: 96.0%

1-benzyl-5-[1-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-one (682811-91-2) → (2R)-2-[(2S)-1-benzyl-2-[(tert-butyldimethylsilanyloxy)methyl]-5-oxopyrrolidin-2-yl]-2-(tert-butyldimethylsilanyloxy)acetaldehyde (682811-72-9)

Guidance literature:

With sodium periodate; silica gel; In dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1021/jo035846a

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2R)-2-[(2S)-1-benzyl-2-[(tert-butyldimethylsilanyloxy)methyl]-5-oxopyrrolidin-2-yl]-2-(tert-butyldimethylsilanyloxy)acetaldehyde (682811-72-9)

Guidance literature:

Multi-step reaction with 5 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

4: CeCl₃*7H₂O; oxalic acid / acetonitrile / 5 h / 40 °C

5: 96 percent / NaIO₄; SiO₂ / CH₂Cl₂; H₂O / 1 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; cerium(III) chloride; ammonium cerium(IV) nitrate; oxalic acid; silica gel; potassium hydride; In tetrahydrofuran; dichloromethane; water; 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 → (2R)-2-[(2S)-1-benzyl-2-[(tert-butyldimethylsilanyloxy)methyl]-5-oxopyrrolidin-2-yl]-2-(tert-butyldimethylsilanyloxy)acetaldehyde (682811-72-9)

Guidance literature:

Multi-step reaction with 6 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

5: CeCl₃*7H₂O; oxalic acid / acetonitrile / 5 h / 40 °C

6: 96 percent / NaIO₄; SiO₂ / CH₂Cl₂; H₂O / 1 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; ammonium cerium(IV) nitrate; oxalic acid; silica gel; potassium hydride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jo035846a

upstream raw materials:

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

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

Downstream raw materials:

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