(2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine

Base Information

• Chemical Name: (2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine
• CAS No.: 943135-40-8
• Molecular Formula: C₂₆H₃₃NO₄
• Molecular Weight: 423.552
• Mol file: 943135-40-8.mol

Synonyms:(2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine

Chemical Property of (2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine

There total 12 articles about (2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine 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) → (2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine (943135-40-8)

Guidance literature:

Multi-step reaction with 11 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

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

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

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

7.1: p-TsOH / methanol / 3 h / 20 °C

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

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

9.2: 2.86 g / tetrahydrofuran / 0.5 h / Heating

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

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

With 1H-imidazole; oxalyl dichloride; methanesulfonamide; AD-mix-β; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Swern oxidation / 2.2: Horner-Wittig reaction / 5.1: Sharpless asymmetric dihydroxylation / 9.2: Horner-Wittig reaction;

DOI:10.1016/j.tetasy.2007.03.022

Reference yield:

(4R,5R)-7-[N-(tert-butoxycarbonyl)amino]-4,5-dibenzyloxy-2-hepten-1-ol (943135-39-5) → (2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine (943135-40-8)

Guidance literature:

dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2007.03.022

Reference yield:

(2S,3R)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxypentanal (943135-46-4) → (2R,3R,4R)-N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-vinylpiperidine (943135-40-8)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 2.86 g / tetrahydrofuran / 0.5 h / Heating

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

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

With sodium hydride; diisobutylaluminium hydride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; 1.2: Horner-Wittig reaction;

DOI:10.1016/j.tetasy.2007.03.022

upstream raw materials:

(4R,5R)-7-[N-(tert-butoxycarbonyl)amino]-4,5-dibenzyloxy-2-hepten-1-ol

(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

Downstream raw materials:

(2R,3R,4R)-(N-tert-butoxycarbonyl-3,4-dibenzyloxy-2-piperidinyl)methanol

3,4-dibenzyloxy-1,5-imino-1,2,5-trideoxy-D-arabino hexitol

D-fagomine