L-Isoleucine, N-[(phenylmethoxy)carbonyl]-, methoxymethyl ester

Base Information

• Chemical Name: L-Isoleucine, N-[(phenylmethoxy)carbonyl]-, methoxymethyl ester
• CAS No.: 802911-32-6
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362

Synonyms:

Chemical Property of L-Isoleucine, N-[(phenylmethoxy)carbonyl]-, methoxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of L-Isoleucine, N-[(phenylmethoxy)carbonyl]-, methoxymethyl ester

There total 1 articles about L-Isoleucine, N-[(phenylmethoxy)carbonyl]-, methoxymethyl 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: 76.0%

N-Cbz-L-Isoleucine (3160-59-6) + chloromethyl methyl ether (107-30-2) → N-Z-isoleucine methoxymethyl ester (802911-32-6)

Guidance literature:

chloromethyl methyl ether; With lithium iodide; In acetonitrile; for 0.333333h; cooling;

N-Cbz-L-Isoleucine; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1002/chem.200400249

Reference yield:

N-Z-isoleucine methoxymethyl ester (802911-32-6) → hormaomycin

Guidance literature:

Multi-step reaction with 15 steps

1.1: H₂; AcOH / Pd/C / ethyl acetate / 1 h / ambient pressure

2.1: EDC; HOAt / CH₂Cl₂ / 0.17 h / 4 °C

2.2: 0.40 g / TMP / CH₂Cl₂ / 2 h / 20 °C

3.1: H₂; AcOH / Pd/C / ethyl acetate / 1 h / ambient pressure

4.1: H₂; AcOH / Pd/C / ethyl acetate / 1 h / ambient pressure

4.2: EDC; HOAt / CH₂Cl₂ / 0.17 h / 4 °C

4.3: 0.220 g / TMP / CH₂Cl₂ / 15 h / 20 °C

5.1: H₂; Et₂NH / Pd/C / acetonitrile / 0.5 h / 20 °C

6.1: EDC; HOAt / CH₂Cl₂; acetonitrile / 0.17 h / 4 °C

6.2: 195 mg / TMP / CH₂Cl₂; acetonitrile / 15 h / 20 °C

7.1: Et₂NH / acetonitrile / 0.5 h / 20 °C

8.1: 185 mg / HATU; HOAt; N,N-diisopropylethylamine / TMP / CH₂Cl₂; acetonitrile / 15 h / 20 °C

9.1: HCl / ethyl acetate / 0.75 h / 20 °C

10.1: 86 mg / HATU; HOAt; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 20 °C

11.1: anisole / trifluoroacetic acid / 2 h / 20 °C

12.1: 19.7 mg / HATU; HOAt; N,N-diisopropylethylamine / TMP / CH₂Cl₂ / 15 h / 20 °C

13.1: TFA / 1 h / 20 °C

14.1: 20.5 mg / HATU; N,N-diisopropylethylamine; TMP / CH₂Cl₂ / 2.5 h / 20 °C

15.1: 13.2 mg / MgBr₂*Et₂O; EtSH / CH₂Cl₂ / 3 h / 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; hydrogen; thymidine 5'-phosphate; acetic acid; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; ethanethiol; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; magnesium bromide; palladium on activated charcoal; thymidine 5'-phosphate; In dichloromethane; ethyl acetate; acetonitrile; trifluoroacetic acid;

DOI:10.1002/chem.200400249

Reference yield:

N-Z-isoleucine methoxymethyl ester (802911-32-6) → C57H73ClN10O15 (872312-02-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: H₂; AcOH / Pd/C / ethyl acetate / 1 h / ambient pressure

2.1: EDC; HOAt / CH₂Cl₂ / 0.17 h / 4 °C

2.2: 0.40 g / TMP / CH₂Cl₂ / 2 h / 20 °C

3.1: H₂; AcOH / Pd/C / ethyl acetate / 1 h / ambient pressure

4.1: H₂; AcOH / Pd/C / ethyl acetate / 1 h / ambient pressure

4.2: EDC; HOAt / CH₂Cl₂ / 0.17 h / 4 °C

4.3: 0.220 g / TMP / CH₂Cl₂ / 15 h / 20 °C

5.1: H₂; Et₂NH / Pd/C / acetonitrile / 0.5 h / 20 °C

6.1: EDC; HOAt / CH₂Cl₂; acetonitrile / 0.17 h / 4 °C

6.2: 195 mg / TMP / CH₂Cl₂; acetonitrile / 15 h / 20 °C

7.1: Et₂NH / acetonitrile / 0.5 h / 20 °C

8.1: 185 mg / HATU; HOAt; N,N-diisopropylethylamine / TMP / CH₂Cl₂; acetonitrile / 15 h / 20 °C

9.1: HCl / ethyl acetate / 0.75 h / 20 °C

10.1: 86 mg / HATU; HOAt; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 20 °C

11.1: anisole / trifluoroacetic acid / 2 h / 20 °C

12.1: 19.7 mg / HATU; HOAt; N,N-diisopropylethylamine / TMP / CH₂Cl₂ / 15 h / 20 °C

13.1: TFA / 1 h / 20 °C

14.1: 20.5 mg / HATU; N,N-diisopropylethylamine; TMP / CH₂Cl₂ / 2.5 h / 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; hydrogen; thymidine 5'-phosphate; acetic acid; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; thymidine 5'-phosphate; In dichloromethane; ethyl acetate; acetonitrile; trifluoroacetic acid;

DOI:10.1002/chem.200400249

upstream raw materials:

N-Cbz-L-Isoleucine

chloromethyl methyl ether

Downstream raw materials:

H-(βMe)Phe-Ile-OMOM

Z-(β-Me)Phe-Ile-OMOM

(2S,3S)-2-{(2S,3R)-2-[(R)-2-Amino-3-((1R,2R)-2-nitro-cyclopropyl)-propionylamino]-3-phenyl-butyrylamino}-3-methyl-pentanoic acid methoxymethyl ester

(2S,3S)-2-{(2S,3R)-2-[(R)-2-((2S,3R)-2-Amino-3-phenyl-butyrylamino)-3-((1R,2R)-2-nitro-cyclopropyl)-propionylamino]-3-phenyl-butyrylamino}-3-methyl-pentanoic acid methoxymethyl ester

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