[(1S,2R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1S,2R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid tert-butyl ester
• CAS No.: 158723-51-4
• Molecular Formula: C₃₀H₄₄N₂O₆Si
• Molecular Weight: 556.775
• Mol file: 158723-51-4.mol

Synonyms:

Chemical Property of [(1S,2R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid tert-butyl ester

There total 8 articles about [(1S,2R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid tert-butyl ester 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:

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → [(1S,2R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid tert-butyl ester (158723-51-4)

Guidance literature:

Multi-step reaction with 7 steps

1: DMAP, NEt₃ / dimethylformamide / 12 h / Ambient temperature

2: DIBAH / toluene / 3 h / -78 °C

3: 82 percent / MgSO₄ / CH₂Cl₂ / 2 h / Ambient temperature

4: 86 percent / diethyl ether; tetrahydrofuran / 0.17 h / -78 °C

5: aq. TiCl₃ / methanol / 0.25 h / Ambient temperature

6: dioxane / 16 h / Ambient temperature

7: 1.) CF₃SO₃CH₃, 2.) methanolic NaBH₄, 3.) aq. CuO-CuCl₂

With dmap; sodium tetrahydroborate; titanium(III) chloride; cupric chloride-cupric oxide; diisobutylaluminium hydride; magnesium sulfate; triethylamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c39940001731

Reference yield:

[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-formyl-ethyl]-carbamic acid tert-butyl ester (154456-41-4) → [(1S,2R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid tert-butyl ester (158723-51-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / MgSO₄ / CH₂Cl₂ / 2 h / Ambient temperature

2: 86 percent / diethyl ether; tetrahydrofuran / 0.17 h / -78 °C

3: aq. TiCl₃ / methanol / 0.25 h / Ambient temperature

4: dioxane / 16 h / Ambient temperature

5: 1.) CF₃SO₃CH₃, 2.) methanolic NaBH₄, 3.) aq. CuO-CuCl₂

With sodium tetrahydroborate; titanium(III) chloride; cupric chloride-cupric oxide; magnesium sulfate; methyl trifluoromethanesulfonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane;

DOI:10.1039/c39940001731

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → [(1S,2R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid tert-butyl ester (158723-51-4)

Guidance literature:

Multi-step reaction with 7 steps

1: DMAP, NEt₃ / dimethylformamide / 12 h / Ambient temperature

2: DIBAH / toluene / 3 h / -78 °C

3: 82 percent / MgSO₄ / CH₂Cl₂ / 2 h / Ambient temperature

4: 86 percent / diethyl ether; tetrahydrofuran / 0.17 h / -78 °C

5: aq. TiCl₃ / methanol / 0.25 h / Ambient temperature

6: dioxane / 16 h / Ambient temperature

7: 1.) CF₃SO₃CH₃, 2.) methanolic NaBH₄, 3.) aq. CuO-CuCl₂

With dmap; sodium tetrahydroborate; titanium(III) chloride; cupric chloride-cupric oxide; diisobutylaluminium hydride; magnesium sulfate; triethylamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c39940001731

upstream raw materials:

N-tert-butyloxycarbonyl-L-serine methyl ester

[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-formyl-ethyl]-carbamic acid tert-butyl ester

tert-butylchlorodiphenylsilane

methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(tert-butoxy)carbonylamino]propanoate