(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
Hs Code.:

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

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

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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:

: 58885-58-8
N-tert-butoxycarbonyl-3-aminopropanol

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

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:

: 943135-44-2
(2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)pentan-2,3-diol

: 100-39-0
benzyl bromide

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

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:

: 943135-37-3
5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)-2-pentene

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

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