7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate

Base Information

• Chemical Name: 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate
• CAS No.: 160806-00-8
• Molecular Formula: C₂₆H₄₂N₂O₈Si
• Molecular Weight: 538.714

Synonyms:7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate

Chemical Property of 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate

There total 9 articles about 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate 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: 53.0%

2-(Trimethylsilyl)ethanol (2916-68-9) + methyl (2RS,4'S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-pentanoate → 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-Nα-benzyloxycarbonyl-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate (160806-00-8) + 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6S)-Nα-benzyloxycarbonyl-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate (478920-12-6)

Guidance literature:

With lithium hexamethyldisilazane; at 0 ℃;

DOI:10.1016/0040-4039(94)88210-X

Reference yield:

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-Nα-benzyloxycarbonyl-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate (160806-00-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 76 percent / SOCl₂ / Heating

2.1: 73 percent / LiAl(OtBu)3H / tetrahydrofuran / -78 °C

3.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

3.2: 76 percent / tetrahydrofuran / -78 - -30 °C

4.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

5.1: H₂ / Pd(OH)2/C / methanol

6.1: NaHCO₃ / tetrahydrofuran; H₂O / 1 h

With thionyl chloride; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; water; 3.2: Wittig-Horner reaction;

DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

Reference yield:

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde (89969-26-6) → 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-Nα-benzyloxycarbonyl-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate (160806-00-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

1.2: 76 percent / tetrahydrofuran / -78 - -30 °C

2.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

3.1: H₂ / Pd(OH)2/C / methanol

4.1: NaHCO₃ / tetrahydrofuran; H₂O / 1 h

With hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; water; 1.2: Wittig-Horner reaction;

DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

upstream raw materials:

2-(Trimethylsilyl)ethanol

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

Downstream raw materials:

methyl [7-methyl(2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate

methyl [7-methyl (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate

7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate

(2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester

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