[(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester

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Chemical Name:[(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester
CAS No.:691871-79-1
Molecular Formula:C₂₁H₃₃NO₅
Molecular Weight:379.497
Hs Code.:

Synonyms:[(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester

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Chemical Property of [(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester

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Technology Process of [(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester

There total 4 articles about [(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester 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: 58.0%

: 117049-14-6
tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate

: 3-(tetrahydropyran-2-yloxy)propylmagnesium bromide

: 691871-79-1
[(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester

Guidance literature:: tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate; With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

3-(tetrahydropyran-2-yloxy)propylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;
DOI:10.1016/j.tetlet.2003.11.103

Reference yield:

: 2900-27-8
(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid

: 691871-79-1
[(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / K₂CO₃ / dimethylformamide / 1 h / 0 - 20 °C

2.1: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

3.1: DMSO; (COCl)2; i-Pr₂NEt / CH₂Cl₂

3.2: 58 percent / tetrahydrofuran / 2 h / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 3.2: Grignard reaction;
DOI:10.1016/j.tetlet.2003.11.103

Reference yield:

: 2935-35-5
(S)-2-phenylglycine

: 691871-79-1
[(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / NaOH / dioxane / 2 h / 0 - 20 °C

2.1: 85 percent / K₂CO₃ / dimethylformamide / 1 h / 0 - 20 °C

3.1: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

4.1: DMSO; (COCl)2; i-Pr₂NEt / CH₂Cl₂

4.2: 58 percent / tetrahydrofuran / 2 h / 20 °C

With sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 4.1: Swern oxidation / 4.2: Grignard reaction;
DOI:10.1016/j.tetlet.2003.11.103