tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate
• CAS No.: 143233-36-7
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.385
• Mol file: 143233-36-7.mol

Synonyms:tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate

Chemical Property of tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate

There total 6 articles about tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate 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: 90.0%

[(1S,2S)-1-Benzyl-2-furan-2-yl-2-(1-methyl-1-trimethylsilanyl-ethoxy)-ethyl]-carbamic acid tert-butyl ester → tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate (143233-36-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0957-4166(03)00218-0

Reference yield:

C18H21NO4 (143233-23-2) → tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate (143233-24-3) + tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate (143233-36-7)

Guidance literature:

C₁₈H₂₁NO₄; With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; ethyl acetate; at 20 ℃; for 0.25h; optical yield given as %de;

DOI:10.1016/j.tet.2009.03.080

Reference yield:

furfural (98-01-1) → tert-butyl (2S)-1-(furan-2-yl)-1-hydroxy-3-phenylpropan-2-ylcarbamate (143233-36-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: R-oxynitrilase (E_.C_. 4.1.2.10) from almond meal / H₂O; various solvent(s) / pH 5.5

2.1: imidazole / dimethylformamide / 0 - 20 °C

3.1: diethyl ether / 1 h / Heating

3.2: NaBH₄; MeOH / diethyl ether / -70 - 20 °C

4.1: 28 percent / NaHCO₃ / CH₂Cl₂; H₂O

5.1: 90 percent / TBAF*3H₂O / tetrahydrofuran

With 1H-imidazole; R-oxynitrilase (E_.C_. 4.1.2.10) from almond meal; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(03)00218-0

upstream raw materials:

furfural

(S)-2-(2'-furyl)-2-hydroxy-acetonitrile

(S)-2-(tert-butyldimethylsilyloxy)-2-(furan-2-yl)acetonitrile

C₁₈H₂₁NO₄