N²-1-benzyl-N-(N-lauroyl-L-alanyl)-γ-D-glutamyl>-N⁶-benzyloxycarbonyl-L-2,6-diaminopimelamic acid

Base Information

• Chemical Name: N²-1-benzyl-N-(N-lauroyl-L-alanyl)-γ-D-glutamyl>-N⁶-benzyloxycarbonyl-L-2,6-diaminopimelamic acid
• CAS No.: 78057-80-4
• Molecular Formula: C₄₂H₆₁N₅O₁₀
• Molecular Weight: 795.974
• Mol file: 78057-80-4.mol

Synonyms:

Chemical Property of N²-1-benzyl-N-(N-lauroyl-L-alanyl)-γ-D-glutamyl>-N⁶-benzyloxycarbonyl-L-2,6-diaminopimelamic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-1-benzyl-N-(N-lauroyl-L-alanyl)-γ-D-glutamyl>-N⁶-benzyloxycarbonyl-L-2,6-diaminopimelamic acid

There total 17 articles about N²-1-benzyl-N-(N-lauroyl-L-alanyl)-γ-D-glutamyl>-N⁶-benzyloxycarbonyl-L-2,6-diaminopimelamic acid 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:

2,6-dicyanopiperidine (41980-31-8) → N2-1-benzyl-N-(N-lauroyl-L-alanyl)-γ-D-glutamyl>-N6-benzyloxycarbonyl-L-2,6-diaminopimelamic acid (78057-80-4,78148-13-7,78513-41-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / ammonium bicarbonate, NH₄OH / 4 h / 100 - 105 °C / autoclave

2: 70 percent / aq. HBr(48percent, d = 1.49) / 36 h / Heating

4: 1.) aq. NaOH, AcOH (pH 5.2), 2.) papain, L-cysteine, KH₂PO₄, Na₂HPO₄ / 2.) water, 24 h, 37 deg C

5: 91 percent / aq. HCl (d = 1.19), AcOH / 24 h / Heating

6: 1.) aq. NaOH (pH 8-9), dicyclohexylamine, 2.) aq. methanesulfonic acid / 1.) 0 deg C --> room temperature, 20 h, 2.) water, EtOAc

7: 89 percent / toluene-p-sulphonic acid / toluene / 5 h / Heating

8: 32 percent / KOH / phenylmethanol / 1.) 40 deg C, 7.5 h, 2.) 20 deg C, 16 h

9: 95 percent / NH₃ / methanol / 144 h / 20 °C / autoclave

10: 99 percent / aq. HCl (d = 1.19), H₂ / palladium-charcoal (3percent) / methanol / 4 h

11: 1.) CuBr₂, aq. NaOH (pH 10 --> 8), 2.) aq. HCl, H₂S (gas) / 1.) water, 20 deg C, 20 h, 2.) MeOH, 22 h

12: 1.) isobutyl chloroformate, Et₃N, 2.) NaOH / 1.) THF, -6 deg C, 20 min, 2.) water, 0 - 20 deg C, 17 h

With hydrogenchloride; potassium hydroxide; ammonium hydroxide; sodium hydroxide; disodium hydrogenphosphate; potassium dihydrogenphosphate; methanesulfonic acid; L-Cysteine; hydrogen sulfide; ammonia; hydrogen bromide; hydrogen; ammonium bicarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; N-cyclohexyl-cyclohexanamine; copper(ll) bromide; papain; isobutyl chloroformate; palladium on activated charcoal; In methanol; toluene; benzyl alcohol;

Reference yield:

5,5'-trimethylenedihydantoin (41980-32-9) → N2-1-benzyl-N-(N-lauroyl-L-alanyl)-γ-D-glutamyl>-N6-benzyloxycarbonyl-L-2,6-diaminopimelamic acid (78057-80-4,78148-13-7,78513-41-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 70 percent / aq. HBr(48percent, d = 1.49) / 36 h / Heating

3: 1.) aq. NaOH, AcOH (pH 5.2), 2.) papain, L-cysteine, KH₂PO₄, Na₂HPO₄ / 2.) water, 24 h, 37 deg C

4: 91 percent / aq. HCl (d = 1.19), AcOH / 24 h / Heating

5: 1.) aq. NaOH (pH 8-9), dicyclohexylamine, 2.) aq. methanesulfonic acid / 1.) 0 deg C --> room temperature, 20 h, 2.) water, EtOAc

6: 89 percent / toluene-p-sulphonic acid / toluene / 5 h / Heating

7: 32 percent / KOH / phenylmethanol / 1.) 40 deg C, 7.5 h, 2.) 20 deg C, 16 h

8: 95 percent / NH₃ / methanol / 144 h / 20 °C / autoclave

9: 99 percent / aq. HCl (d = 1.19), H₂ / palladium-charcoal (3percent) / methanol / 4 h

10: 1.) CuBr₂, aq. NaOH (pH 10 --> 8), 2.) aq. HCl, H₂S (gas) / 1.) water, 20 deg C, 20 h, 2.) MeOH, 22 h

11: 1.) isobutyl chloroformate, Et₃N, 2.) NaOH / 1.) THF, -6 deg C, 20 min, 2.) water, 0 - 20 deg C, 17 h

With hydrogenchloride; potassium hydroxide; sodium hydroxide; disodium hydrogenphosphate; potassium dihydrogenphosphate; methanesulfonic acid; L-Cysteine; hydrogen sulfide; ammonia; hydrogen bromide; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; N-cyclohexyl-cyclohexanamine; copper(ll) bromide; papain; isobutyl chloroformate; palladium on activated charcoal; In methanol; toluene; benzyl alcohol;

Reference yield:

2,6-diaminopimelic acid (922-54-3,2577-62-0,14289-34-0,17121-19-6,583-93-7,1356383-43-1) → N2-1-benzyl-N-(N-lauroyl-L-alanyl)-γ-D-glutamyl>-N6-benzyloxycarbonyl-L-2,6-diaminopimelamic acid (78057-80-4,78148-13-7,78513-41-4)

Guidance literature:

Multi-step reaction with 10 steps

2: 1.) aq. NaOH, AcOH (pH 5.2), 2.) papain, L-cysteine, KH₂PO₄, Na₂HPO₄ / 2.) water, 24 h, 37 deg C

3: 91 percent / aq. HCl (d = 1.19), AcOH / 24 h / Heating

4: 1.) aq. NaOH (pH 8-9), dicyclohexylamine, 2.) aq. methanesulfonic acid / 1.) 0 deg C --> room temperature, 20 h, 2.) water, EtOAc

5: 89 percent / toluene-p-sulphonic acid / toluene / 5 h / Heating

6: 32 percent / KOH / phenylmethanol / 1.) 40 deg C, 7.5 h, 2.) 20 deg C, 16 h

7: 95 percent / NH₃ / methanol / 144 h / 20 °C / autoclave

8: 99 percent / aq. HCl (d = 1.19), H₂ / palladium-charcoal (3percent) / methanol / 4 h

9: 1.) CuBr₂, aq. NaOH (pH 10 --> 8), 2.) aq. HCl, H₂S (gas) / 1.) water, 20 deg C, 20 h, 2.) MeOH, 22 h

10: 1.) isobutyl chloroformate, Et₃N, 2.) NaOH / 1.) THF, -6 deg C, 20 min, 2.) water, 0 - 20 deg C, 17 h

With hydrogenchloride; potassium hydroxide; sodium hydroxide; disodium hydrogenphosphate; potassium dihydrogenphosphate; methanesulfonic acid; L-Cysteine; hydrogen sulfide; ammonia; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; N-cyclohexyl-cyclohexanamine; copper(ll) bromide; papain; isobutyl chloroformate; palladium on activated charcoal; In methanol; toluene; benzyl alcohol;

upstream raw materials:

N⁶-benzyloxycarbonyl-L-2,6-diaminopimelamic acid

O¹-benzyl-N-(N-lauroyl-L-alanyl)-D-glutamic acid

2,6-dicyanopiperidine

5,5'-trimethylenedihydantoin

Downstream raw materials:

RP 56142

Refernces