(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol

Base Information

• Chemical Name: (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol
• CAS No.: 147165-87-5
• Molecular Formula: C₂₉H₃₇NO₂Si
• Molecular Weight: 459.704
• Mol file: 147165-87-5.mol

Synonyms:(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol

Chemical Property of (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol

There total 4 articles about (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol 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: 91.0%

(2S,3S)-3-Benzylamino-hex-5-ene-1,2-diol + tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol (147165-87-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; 1.) -40 deg C, 1 h, 2.) up to 0 deg C;

Reference yield:

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol (147165-87-5)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 2 h / -30 °C

2: 77 percent / Zn, CuSO₄, glacial acetic acid / H₂O / 1 h / 70 °C

3: 86 percent / trifluoroacetic acid / H₂O; acetonitrile / 8 h / 20 °C

4: 91 percent / imidazole / dimethylformamide / 1.) -40 deg C, 1 h, 2.) up to 0 deg C

With 1H-imidazole; copper(II) sulfate; acetic acid; trifluoroacetic acid; zinc; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

*,R*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine (147165-81-9) → (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol (147165-87-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / Zn, CuSO₄, glacial acetic acid / H₂O / 1 h / 70 °C

2: 86 percent / trifluoroacetic acid / H₂O; acetonitrile / 8 h / 20 °C

3: 91 percent / imidazole / dimethylformamide / 1.) -40 deg C, 1 h, 2.) up to 0 deg C

With 1H-imidazole; copper(II) sulfate; acetic acid; trifluoroacetic acid; zinc; In water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

tert-butylchlorodiphenylsilane

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

*,R^*)>-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine

*,R^*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine