5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene

Base Information

• Chemical Name: 5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene
• CAS No.: 943135-37-3
• Molecular Formula: C₁₆H₃₃NO₃Si
• Molecular Weight: 315.528
• Mol file: 943135-37-3.mol

Synonyms:5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene

Chemical Property of 5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene

There total 1 articles about 5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene 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-butoxycarbonyl-3-aminopropanol (58885-58-8) → 5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene (943135-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 2.86 g / tetrahydrofuran / 1 h / -50 - 20 °C

3.1: 99 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C

4.1: 89 percent / imidazole / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 2.2: Horner-Wittig reaction;

DOI:10.1016/j.tetasy.2007.03.022

Reference yield:

5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene (943135-37-3) → D-fagomine (53185-12-9,475630-67-2,637771-88-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

2.1: NaH / tetrahydrofuran / 1.5 h / 0 °C

2.2: tetrabutylammonium iodide / tetrahydrofuran / 4 h / 20 °C

3.1: p-TsOH / methanol / 3 h / 20 °C

4.1: IBX / tetrahydrofuran; dimethylsulfoxide / 4 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

5.2: 2.86 g / tetrahydrofuran / 0.5 h / Heating

6.1: DIBAL-H / tetrahydrofuran / 5 h / 20 °C

7.1: PdCl₂(MeCN)2 / tetrahydrofuran / 3 h / 20 °C

8.1: O₃ / CH₂Cl₂; methanol / -78 °C

8.2: NaBH₄ / CH₂Cl₂; methanol / -78 - 20 °C

9.1: aq. HCl / methanol / 5 h / 70 °C

10.1: H₂ / Pd/C / acetic acid / 48 h / 20 °C

With hydrogenchloride; methanesulfonamide; AD-mix-β; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 5.2: Horner-Wittig reaction;

DOI:10.1016/j.tetasy.2007.03.022

Reference yield:

5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene (943135-37-3) → (2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine (943135-40-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

2.1: NaH / tetrahydrofuran / 1.5 h / 0 °C

2.2: tetrabutylammonium iodide / tetrahydrofuran / 4 h / 20 °C

3.1: p-TsOH / methanol / 3 h / 20 °C

4.1: IBX / tetrahydrofuran; dimethylsulfoxide / 4 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

5.2: 2.86 g / tetrahydrofuran / 0.5 h / Heating

6.1: DIBAL-H / tetrahydrofuran / 5 h / 20 °C

7.1: PdCl₂(MeCN)2 / tetrahydrofuran / 3 h / 20 °C

With methanesulfonamide; AD-mix-β; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; water; dimethyl sulfoxide; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 5.2: Horner-Wittig reaction;

DOI:10.1016/j.tetasy.2007.03.022

upstream raw materials:

N-tert-butoxycarbonyl-3-aminopropanol

Downstream raw materials:

(2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxy-1-(tert-butyl-dimethylsilyloxy)pentane

(2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxypentan-1-ol

(2S,3R)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxypentanal

ethyl (4R,5R)-7-[N-(tert-butoxycarbonyl)amino]-4,5-dibenzyloxy-2-heptenoate