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

Base Information

• Chemical Name: (2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxy-1-(tert-butyl-dimethylsilyloxy)pentane
• CAS No.: 943135-45-3
• Molecular Formula: C₃₀H₄₇NO₅Si
• Molecular Weight: 529.792
• Mol file: 943135-45-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxy-1-(tert-butyl-dimethylsilyloxy)pentane 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)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxy-1-(tert-butyl-dimethylsilyloxy)pentane (943135-45-3)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; oxalyl dichloride; methanesulfonamide; AD-mix-β; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Swern oxidation / 2.2: Horner-Wittig reaction / 5.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetasy.2007.03.022

Reference yield:

(2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)pentan-2,3-diol (943135-44-2) + benzyl bromide (100-39-0) → (2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxy-1-(tert-butyl-dimethylsilyloxy)pentane (943135-45-3)

Guidance literature:

(2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)pentan-2,3-diol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 4h; Further stages.;

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)-5-[N-(tert-butoxycarbonyl)amino]-2,3-dibenzyloxy-1-(tert-butyl-dimethylsilyloxy)pentane (943135-45-3)

Guidance literature:

Multi-step reaction with 2 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

With methanesulfonamide; AD-mix-β; sodium hydride; In tetrahydrofuran; water; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetasy.2007.03.022

upstream raw materials:

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

benzyl bromide

(E)-tert-butyl (5-hydroxypent-3-en-1-yl)carbamate

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

Downstream raw materials:

(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

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