(R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate

Base Information

• Chemical Name: (R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate
• CAS No.: 1092363-37-5
• Molecular Formula: C₃₆H₃₇N₃O₄S₃
• Molecular Weight: 671.905
• Mol file: 1092363-37-5.mol

Synonyms:(R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate

Chemical Property of (R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate

There total 8 articles about (R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate 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:

(R)-2-(2-((tert-butoxycarbonylamino)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid (1033814-13-9) → (R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate (1092363-37-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / 0.08 h

2.1: dmap / dichloromethane / 0.08 h

2.2: 1 h

With hydrogenchloride; dmap; In dichloromethane;

DOI:10.1021/jm200432a

Reference yield:

2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide (182120-82-7) → (R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate (1092363-37-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1 h / 0 - 20 °C

2.1: sodium hydrogencarbonate / methanol / 1 h / 70 °C / pH 5.95 / Inert atmosphere; phosphate buffer

3.1: hydrogenchloride / 0.08 h

4.1: dmap / dichloromethane / 0.08 h

4.2: 1 h

With hydrogenchloride; dmap; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; In methanol; dichloromethane;

DOI:10.1021/jm200432a

Reference yield:

2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxylic acid (71904-80-8) → (R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate (1092363-37-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C

1.2: 2 h / 20 °C

2.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1 h / 0 - 20 °C

3.1: sodium hydrogencarbonate / methanol / 1 h / 70 °C / pH 5.95 / Inert atmosphere; phosphate buffer

4.1: hydrogenchloride / 0.08 h

5.1: dmap / dichloromethane / 0.08 h

5.2: 1 h

With hydrogenchloride; dmap; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm200432a

upstream raw materials:

(R)-2-(2-((tert-butoxycarbonylamino)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

(3S,4E)-3-hydroxy-1-((4R)-4-isopropyl-2-thioxothiazolidin-3-yl)-7-tritylsulfanyl-hept-4-en-1-one

triphenylmethanethiol

2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxylic acid

Downstream raw materials:

largazole

(5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione

C₅₅H₅₄N₄O₇S₃

C₄₀H₄₄N₄O₅S₃