[3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl ester

Base Information

• Chemical Name: [3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl ester
• CAS No.: 342655-66-7
• Molecular Formula: C₃₆H₆₄N₂O₃SSi
• Molecular Weight: 633.067
• Mol file: 342655-66-7.mol

Synonyms:[3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl ester

Chemical Property of [3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl ester

There total 5 articles about [3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl 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: 33.0%

phenylcarbonochloridothioate (1005-56-7) + N-[1-aminomethyl-2-(tert-butyl-dimethyl-silanyloxy)-heptadec-3-enyl]-2,2-dimethyl-propionamide (342655-62-3) → [3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl ester (342655-66-7)

Guidance literature:

With pyridine; In tetrahydrofuran; at -78 - -20 ℃;

DOI:10.1016/j.bmcl.2003.08.020

Reference yield:

2-N-pivaloyl-3-O-t-butyldimethylsilyl-D-erythro-sphingosine (342649-70-1) → [3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl ester (342655-66-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / Py*SO₃; Et₃N; DMSO / tetrahydrofuran / 20 °C

2: 98 percent / NH₂OH*HCl; i-Pr₂NEt / tetrahydrofuran / 20 °C

3: 74 percent / pyridine / tetrahydrofuran / 0 °C

4: 58 percent / NaBH₄ / ethanol / -20 °C

5: 33 percent / pyridine / tetrahydrofuran / -78 - -20 °C

With pyridine; sodium tetrahydroborate; hydroxylamine hydrochloride; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol;

DOI:10.1016/j.bmcl.2003.08.020

Reference yield:

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-heptadec-3-enyl]-2,2-dimethyl-propionamide (342655-65-6) → [3-(tert-butyl-dimethyl-silanyloxy)-2-(2,2-dimethyl-propionylamino)-octadec-4-enyl]-thiocarbamic acid O-phenyl ester (342655-66-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / NH₂OH*HCl; i-Pr₂NEt / tetrahydrofuran / 20 °C

2: 74 percent / pyridine / tetrahydrofuran / 0 °C

3: 58 percent / NaBH₄ / ethanol / -20 °C

4: 33 percent / pyridine / tetrahydrofuran / -78 - -20 °C

With pyridine; sodium tetrahydroborate; hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol;

DOI:10.1016/j.bmcl.2003.08.020

upstream raw materials:

phenylcarbonochloridothioate

N-[1-aminomethyl-2-(tert-butyl-dimethyl-silanyloxy)-heptadec-3-enyl]-2,2-dimethyl-propionamide

2-N-pivaloyl-3-O-t-butyldimethylsilyl-D-erythro-sphingosine

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-heptadec-3-enyl]-2,2-dimethyl-propionamide