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

Base Information

• Chemical Name: methyl [7-methyl (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate
• CAS No.: 478920-26-2
• Molecular Formula: C₃₁H₄₆N₄O₁₂
• Molecular Weight: 666.726
• Mol file: 478920-26-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about methyl [7-methyl (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate 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:

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde (89969-26-6) → methyl [7-methyl (2S,6R)-Nα-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate (478920-26-2)

Guidance literature:

Multi-step reaction with 8 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: TBAF / tetrahydrofuran / 20 °C

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

7.1: H₂ / 10percent Pd/C / methanol

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

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; 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) → methyl [7-methyl (2S,6R)-Nα-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate (478920-26-2)

Guidance literature:

Multi-step reaction with 9 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: TBAF / tetrahydrofuran / 20 °C

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

8.1: H₂ / 10percent Pd/C / methanol

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

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; 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

Reference yield:

(2R,6S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester (82361-46-4) → methyl [7-methyl (2S,6R)-Nα-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate (478920-26-2)

Guidance literature:

Multi-step reaction with 3 steps

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

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; 10percent Pd/C; In methanol; dichloromethane;

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

(2R,6S)-6-Amino-2-tert-butoxycarbonylamino-6-((R)-1-methoxycarbonyl-ethylcarbamoyl)-hexanoic acid methyl ester

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

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

Refernces