(5S,11S,14S)-2-Benzyloxycarbonylamino-11-hydroxymethyl-5-isopropyl-3,6,9,12-tetraoxo-1,4,7,10,13-pentaaza-tricyclo[14.6.1.0^17,22]tricosa-16⁽²³⁾,17⁽²²⁾,18,20-tetraene-14-carboxylic acid methyl ester

Base Information

• Chemical Name: (5S,11S,14S)-2-Benzyloxycarbonylamino-11-hydroxymethyl-5-isopropyl-3,6,9,12-tetraoxo-1,4,7,10,13-pentaaza-tricyclo[14.6.1.0^17,22]tricosa-16⁽²³⁾,17⁽²²⁾,18,20-tetraene-14-carboxylic acid methyl ester
• CAS No.: 145396-91-4
• Molecular Formula: C₃₂H₃₈N₆O₉
• Molecular Weight: 650.689

Synonyms:

Chemical Property of (5S,11S,14S)-2-Benzyloxycarbonylamino-11-hydroxymethyl-5-isopropyl-3,6,9,12-tetraoxo-1,4,7,10,13-pentaaza-tricyclo[14.6.1.0^17,22]tricosa-16⁽²³⁾,17⁽²²⁾,18,20-tetraene-14-carboxylic acid methyl ester

Chemical Property:

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Useful:

Technology Process of (5S,11S,14S)-2-Benzyloxycarbonylamino-11-hydroxymethyl-5-isopropyl-3,6,9,12-tetraoxo-1,4,7,10,13-pentaaza-tricyclo[14.6.1.0^17,22]tricosa-16⁽²³⁾,17⁽²²⁾,18,20-tetraene-14-carboxylic acid methyl ester

There total 2 articles about (5S,11S,14S)-2-Benzyloxycarbonylamino-11-hydroxymethyl-5-isopropyl-3,6,9,12-tetraoxo-1,4,7,10,13-pentaaza-tricyclo[14.6.1.0^17,22]tricosa-16⁽²³⁾,17⁽²²⁾,18,20-tetraene-14-carboxylic acid methyl 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:

(S)-2-((S)-2-Amino-3-hydroxy-propionylamino)-3-(1-{benzyloxycarbonylamino-[(S)-2-methyl-1-(pentafluorophenyloxycarbonylmethyl-carbamoyl)-propylcarbamoyl]-methyl}-1H-indol-3-yl)-propionic acid methyl ester → (5S,11S,14S)-2-Benzyloxycarbonylamino-11-hydroxymethyl-5-isopropyl-3,6,9,12-tetraoxo-1,4,7,10,13-pentaaza-tricyclo[14.6.1.017,22]tricosa-16(23),17(22),18,20-tetraene-14-carboxylic acid methyl ester (145396-91-4)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; Yield given;

DOI:10.1039/c39920001353

Reference yield:

(S)-3-(1-{Benzyloxycarbonylamino-[(S)-2-methyl-1-(pentafluorophenyloxycarbonylmethyl-carbamoyl)-propylcarbamoyl]-methyl}-1H-indol-3-yl)-2-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propionylamino)-propionic acid methyl ester (145396-90-3,145511-90-6) → (5S,11S,14S)-2-Benzyloxycarbonylamino-11-hydroxymethyl-5-isopropyl-3,6,9,12-tetraoxo-1,4,7,10,13-pentaaza-tricyclo[14.6.1.017,22]tricosa-16(23),17(22),18,20-tetraene-14-carboxylic acid methyl ester (145396-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane / 1 h / 20 °C

2: aq. NaHCO₃ / CH₂Cl₂

With hydrogenchloride; sodium hydrogencarbonate; In 1,4-dioxane; dichloromethane;

DOI:10.1039/c39920001353

Reference yield:

(5S,11S,14S)-2-Benzyloxycarbonylamino-11-hydroxymethyl-5-isopropyl-3,6,9,12-tetraoxo-1,4,7,10,13-pentaaza-tricyclo[14.6.1.017,22]tricosa-16(23),17(22),18,20-tetraene-14-carboxylic acid methyl ester (145396-91-4) → lyciumin A (125708-06-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂ / Pd/C / dimethylformamide / 2 h

2: 64 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) / dimethylformamide

3: 100 percent / aq. LiOH / dimethylformamide / 2 h / 20 °C

With lithium hydroxide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1039/c39920001353

upstream raw materials:

(S)-3-(1-{Benzyloxycarbonylamino-[(S)-2-methyl-1-(pentafluorophenyloxycarbonylmethyl-carbamoyl)-propylcarbamoyl]-methyl}-1H-indol-3-yl)-2-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propionylamino)-propionic acid methyl ester

Downstream raw materials:

lyciumin A

C₄₃H₅₃N₉O₁₂

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