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

Base Information

• Chemical Name: (1S,4S,5R,6R)-2-benzyl-5,6-bis(tert-butyldimethylsilanyloxy)-1-[(tert-butyldimethylsilanyloxy)methyl]-2-azabicyclo[2.2.1]heptan-3-one
• CAS No.: 682811-73-0
• Molecular Formula: C₃₂H₅₉NO₄Si₃
• Molecular Weight: 606.081
• Mol file: 682811-73-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (1S,4S,5R,6R)-2-benzyl-5,6-bis(tert-butyldimethylsilanyloxy)-1-[(tert-butyldimethylsilanyloxy)methyl]-2-azabicyclo[2.2.1]heptan-3-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: 86.0%

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) → (1S,4S,5R,6R)-2-benzyl-5,6-bis(tert-butyldimethylsilanyloxy)-1-[(tert-butyldimethylsilanyloxy)methyl]-2-azabicyclo[2.2.1]heptan-3-one (682811-73-0) + (1S,4S,5S,6R)-2-benzyl-5,6-bis(tert-butyldimethylsilanyloxy)-1-[(tert-butyldimethylsilanyloxy)methyl]-2-azabicyclo[2.2.1]heptan-3-one

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

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 → (1S,4S,5R,6R)-2-benzyl-5,6-bis(tert-butyldimethylsilanyloxy)-1-[(tert-butyldimethylsilanyloxy)methyl]-2-azabicyclo[2.2.1]heptan-3-one (682811-73-0)

Guidance literature:

Multi-step reaction with 7 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

7: 86 percent / DIPEA / CH₂Cl₂ / 20 °C

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

DOI:10.1021/jo035846a

Reference yield:

(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 (682811-77-4) → (1S,4S,5R,6R)-2-benzyl-5,6-bis(tert-butyldimethylsilanyloxy)-1-[(tert-butyldimethylsilanyloxy)methyl]-2-azabicyclo[2.2.1]heptan-3-one (682811-73-0)

Guidance literature:

Multi-step reaction with 6 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

6: 86 percent / DIPEA / CH₂Cl₂ / 20 °C

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

DOI:10.1021/jo035846a

upstream raw materials:

t-butyldimethylsiyl triflate

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

(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