(2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide

Base Information

• Chemical Name: (2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide
• CAS No.: 1383580-56-0
• Molecular Formula: C₃₇H₅₇N₅O₈
• Molecular Weight: 699.888
• Mol file: 1383580-56-0.mol

Synonyms:(2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide

Chemical Property of (2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide

There total 4 articles about (2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide 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: 69.0%

(2S,4S)-N-((6R,9R,12S,15S,16R,Z)-6-(4-(tert-butoxy)benzyl)-3-ethylidene-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide → (2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide (1383580-56-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/acs.joc.9b03516

Reference yield:

C48H75N5O10 → (2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide (1383580-56-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane; tetrahydrofuran / 0.5 h / 50 °C / Inert atmosphere

2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 2 h / 20 °C

3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 16 h / 0 - 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C

With dmap; 10 wt% Pd(OH)2 on carbon; 2-methyl-6-nitrobenzoic anhydride; hydrogen; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/acs.joc.9b03516

Reference yield:

C41H67N5O9 → (2S,4S)-N-((6R,9R,12S,15S,16R,Z)-3-ethylidene-6-(4-hydroxybenzyl)-12-isobutyl-9-isopropyl-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl)-2,4-dimethylheptanamide (1383580-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; methanesulfonyl chloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C

With methanesulfonyl chloride; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/acs.joc.9b03516

Downstream raw materials:

L-Leu-L-FDLA

D-val-D-FDLA

C₃₃H₃₉N₉O₁₃

(R)-valine hydrochloride

Refernces