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

Base Information

• Chemical Name: 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6S)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate
• CAS No.: 478920-23-9
• Molecular Formula: C₃₂H₅₁N₃O₁₁Si
• Molecular Weight: 681.856
• Mol file: 478920-23-9.mol

Synonyms:

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

There total 11 articles about 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6S)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-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:

2-(Trimethylsilyl)ethanol (2916-68-9) → 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6S)-Nα-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate (478920-23-9)

Guidance literature:

Multi-step reaction with 3 steps

1: LiHMDS / tetrahydrofuran / 0 °C

2: H₂ / 10percent Pd/C / methanol

3: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane;

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,6S)-Nα-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate (478920-23-9)

Guidance literature:

Multi-step reaction with 6 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

5.1: H₂ / 10percent Pd/C / methanol

6.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 1.2: Wittig-Horner reaction;

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

Reference yield:

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester (58456-26-1) → 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6S)-Nα-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelate (478920-23-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 73 percent / LiAl(OtBu)3H / tetrahydrofuran / -78 °C

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

2.2: 76 percent / tetrahydrofuran / -78 - -30 °C

3.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

4.1: H₂ / Pd(OH)2/C / methanol

5.1: NaHCO₃ / tetrahydrofuran; H₂O / 1 h

6.1: H₂ / 10percent Pd/C / methanol

7.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 2.2: Wittig-Horner reaction;

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

upstream raw materials:

N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester

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

Downstream raw materials:

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-{(2R)-propionyl-[L-alanyl-(D-isoglutamyl α-methyl ester)-(7-methyl)-1-(2-trimethylsilylethyl) (2S,6S)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate]-2-yl}-β-D-glucopyranose

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

Refernces