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

Base Information

• Chemical Name: methyl [7-methyl(2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate
• CAS No.: 160579-14-6
• Molecular Formula: C₂₅H₃₇N₃O₉
• Molecular Weight: 523.583
• Mol file: 160579-14-6.mol

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

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

There total 13 articles about methyl [7-methyl(2S,6R)-N^α-benzyloxycarbonyl-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: 33.0%

(Z)-(S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-6-((R)-1-methoxycarbonyl-ethylcarbamoyl)-hex-2-enoic acid methyl ester (160806-01-9) → methyl [7-methyl(2S,6R)-Nα-benzyloxycarbonyl-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate (160579-14-6) + (2S,6S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-6-((R)-1-methoxycarbonyl-ethylcarbamoyl)-hexanoic acid methyl ester

Guidance literature:

With hydrogen; ClO4; (2S,3S)-2,3-bis(diphenylphosphino)butane; In tetrahydrofuran; acetic acid; at 25 ℃; under 2068.6 Torr; Yields of byproduct given;

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

Reference yield:

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → methyl [7-methyl(2S,6R)-Nα-benzyloxycarbonyl-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate (160579-14-6)

Guidance literature:

Multi-step reaction with 8 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

7.1: TBAF / tetrahydrofuran / 20 °C

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

With 4-methyl-morpholine; thionyl chloride; 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; 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) → methyl [7-methyl(2S,6R)-Nα-benzyloxycarbonyl-Nε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate (160579-14-6)

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: TBAF / tetrahydrofuran / 20 °C

6.1: 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

upstream raw materials:

(Z)-(S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-6-((R)-1-methoxycarbonyl-ethylcarbamoyl)-hex-2-enoic acid methyl ester

D-alanine methyl ester hydrochloride

(2R,6S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester

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

Downstream raw materials:

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