N²-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester

Base Information

• Chemical Name: N²-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester
• CAS No.: 1467710-25-3
• Molecular Formula: C₃₆H₄₈N₄O₁₁
• Molecular Weight: 716.758

Synonyms:N²-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester

Chemical Property of N²-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester

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Technology Process of N²-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester

There total 3 articles about N²-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester 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: 98.0%

L-[1,2,3-13C3, 15N]alanyl-D-α-glutamine phenylmethyl ester hydrochloride (1467710-19-5) + C21H29NO8 (1467710-22-0) → N2-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-13C3, 15N]alanyl-D-α-glutamine phenylmethyl ester (1467710-25-3)

Guidance literature:

L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester hydrochloride; C₂₁H₂₉NO₈; With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; In ethyl acetate;

With dicyclohexyl-carbodiimide; at 20 ℃; for 2.5h;

DOI:10.1002/jlcr.3078

Reference yield:

D-Glutaminsaeure-α-amid-γ-benzylester (71811-14-8,80064-48-8) → N2-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-13C3, 15N]alanyl-D-α-glutamine phenylmethyl ester (1467710-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 4-methyl-morpholine / N,N-dimethyl-formamide; ethyl acetate / -10 °C

1.3: 0.5 h / -5 °C

2.1: hydrogenchloride / di-isopropyl ether / 20 °C

3.1: 1-hydroxy-pyrrolidine-2,5-dione; triethylamine / ethyl acetate

3.2: 2.5 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; In di-isopropyl ether; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/jlcr.3078

Reference yield:

N-[(1,1-dimethylethoxy)carbonyl]-L-[1,2,3-13C3, 15N]alanyl-D-α-glutamine phenylmethyl ester (1467710-17-3) → N2-[N-(N-acetyl)-4,6-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-13C3, 15N]alanyl-D-α-glutamine phenylmethyl ester (1467710-25-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / di-isopropyl ether / 20 °C

2.1: 1-hydroxy-pyrrolidine-2,5-dione; triethylamine / ethyl acetate

2.2: 2.5 h / 20 °C

With hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; In di-isopropyl ether; ethyl acetate;

DOI:10.1002/jlcr.3078

upstream raw materials:

D-Glutaminsaeure-α-amid-γ-benzylester

N-[(1,1-dimethylethoxy)carbonyl]-L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester

L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester hydrochloride

C₂₁H₂₉NO₈

Downstream raw materials:

N²-[N-(N-acetyl)-1-O-(phenylmethyl)-α-muramoyl]-L-[1,2,3-¹³C₃, ¹⁵N]alanyl-D-α-glutamine phenylmethyl ester

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