Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester
• CAS No.: 199786-64-6
• Molecular Formula: C₄₅H₅₃NO₄Si₂
• Molecular Weight: 728.091
• Mol file: 199786-64-6.mol

Synonyms:Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester

Chemical Property of Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester

There total 8 articles about Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl 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: 80.0%

Triphenylsilyl chloride (76-86-8) + Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester (199786-66-8) → Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester (199786-64-6)

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(97)10166-6

Reference yield:

N-benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-D-serinal (199786-65-7) → Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester (199786-64-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn; AlCl₃ / tetrahydrofuran / 0.5 h / 20 °C

2: 80 percent / CH₂Cl₂; pyridine / 20 h

With aluminium trichloride; zinc; In tetrahydrofuran; pyridine; dichloromethane;

Reference yield:

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate (123639-56-5,131110-76-4,144001-42-3) → Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-triphenylsilanyloxy-pent-4-enyl]-carbamic acid benzyl ester (199786-64-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent

2: 98 percent / imidazole / CH₂Cl₂; dimethylformamide

3: 81 percent / LiBH₄ / tetrahydrofuran; ethanol

4: 90 percent / NaOCl, TEMPO, NaBr / toluene; ethyl acetate; H₂O / 0 °C

5: SnCl₂*2H₂O, sodium iodide / dimethylformamide / Ambient temperature

6: 80 percent / pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium borohydride; sodium iodide; sodium bromide; tin(ll) chloride; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(97)10166-6

upstream raw materials:

Triphenylsilyl chloride

Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester

N-benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-D-serinal

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate

Downstream raw materials:

Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-oxo-2-triphenylsilanyloxy-pentyl]-carbamic acid benzyl ester

Benzyl-[(1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-2-triphenylsilanyloxy-pentyl]-carbamic acid benzyl ester