methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH

Base Information

Chemical Name:methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH
CAS No.:403852-44-8
Molecular Formula:C₆₄H₉₀N₁₀O₂₂
Molecular Weight:1351.47
Hs Code.:

Synonyms:methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH

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Chemical Property of methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH

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Technology Process of methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH

There total 23 articles about methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH 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: 34.0%

: 404002-11-5
methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]glycine pentafluorophenyl ester

: 150854-44-7
H-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH

: 403852-44-8
methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH

Guidance literature:: With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 40h;
DOI:10.1021/jm010352w

Reference yield:

: 13139-15-6,53296-34-7
N-tert-butoxycarbonyl-L-leucine

: 403852-44-8
methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH

Guidance literature:: Multi-step reaction with 8 steps

1.1: HOBT; DCC / tetrahydrofuran / 0.5 h / 0 °C

1.2: 87 percent / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

2.1: 85 percent / HCO₂H / 6 h / 20 °C

3.1: HOBT; DCC / tetrahydrofuran / 0.5 h / 0 °C

3.2: 77 percent / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

4.1: 85 percent / H₂ / 10percent Pd/C / ethanol / 2 h / 2068.65 Torr

5.1: HOBT; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 0.5 h / 0 °C

5.2: 66 percent / tetrahydrofuran; dimethylformamide / 74 h / 0 - 20 °C

6.1: H₂ / 10percent Pd/C / acetic acid / 6 h

7.1: 95 mg / TFA / 1 h / 20 °C

8.1: 34 percent / NEt₃ / tetrahydrofuran; dimethylformamide / 40 h / 20 °C

With formic acid; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; ethanol; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm010352w

Reference yield:

: 1738-69-8
L-Leucine benzyl ester

: 403852-44-8
methyl N-[β-D-glucopyranuronate-3-nitrobenzyloxycarbonyl]-Gly-Ile-Leu-Gly-Phe-Val-Phe-Thr-Leu-OH

Guidance literature:: Multi-step reaction with 10 steps

1.1: HOBT; DCC / tetrahydrofuran / 0.5 h / 0 °C

1.2: 84 percent / tetrahydrofuran; dimethylformamide / 18 h / 0 - 20 °C

2.1: 87 percent / HCO₂H / 6 h / 20 °C

3.1: HOBT; DCC / tetrahydrofuran / 0.5 h / 0 °C

3.2: 77 percent / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

4.1: 82 percent / HCO₂H / 6 h / 20 °C

5.1: HOBT; DCC / tetrahydrofuran / 0.5 h / 0 °C

5.2: 70 percent / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

6.1: 90 percent / HCO₂H / 6 h / 20 °C

7.1: HOBT; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 0.5 h / 0 °C

7.2: 66 percent / tetrahydrofuran; dimethylformamide / 74 h / 0 - 20 °C

8.1: H₂ / 10percent Pd/C / acetic acid / 6 h

9.1: 95 mg / TFA / 1 h / 20 °C

10.1: 34 percent / NEt₃ / tetrahydrofuran; dimethylformamide / 40 h / 20 °C

With formic acid; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm010352w