(1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate

Base Information

• Chemical Name: (1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate
• CAS No.: 1596364-75-8
• Molecular Formula: C₄₂H₄₆N₆O₄SSi
• Molecular Weight: 759.017
• Mol file: 1596364-75-8.mol

Synonyms:(1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate

Chemical Property of (1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate

There total 12 articles about (1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate 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: 81.0%

4-bromo-2,6-dimethylpyridine (5093-70-9) + (1S,2R,3S,4R)-methyl 4-((2-amino-5-(benzo[d]thiazol-2-yl)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate (1596364-74-7) → (1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate (1596364-75-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium phenoxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100 ℃; for 18h;

Reference yield:

2-(1R,2S,3R,4R)-3-hydroxy-4-(hydroxymethyl)-2-methoxycyclopentylisoindoline-1,3-dione (1596364-65-6) → (1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate (1596364-75-8)

Guidance literature:

Multi-step reaction with 11 steps

1: dmap / N,N-dimethyl-formamide / 22 h / 0 - 20 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C

3: pyridinium p-toluenesulfonate / ethanol / 18 h / 50 °C

4: sodium periodate; ruthenium(III) trichloride hydrate / water; tetrachloromethane; acetonitrile / 1 h

5: diazomethyl-trimethyl-silane / toluene / 0 - 20 °C

6: hydrazine / ethanol; diethyl ether / 18 h / 20 °C

7: triethylamine / ethanol / 18 h / 80 °C

8: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

9: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C

10: ammonium hydroxide / 1,4-dioxane; water / 1 h / 80 °C / Sealed tube

11: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium phenoxide / 1,4-dioxane / 18 h / 100 °C

With 1H-imidazole; dmap; ammonium hydroxide; sodium periodate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ruthenium(III) trichloride hydrate; sodium phenoxide; pyridinium p-toluenesulfonate; caesium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; hydrazine; diazomethyl-trimethyl-silane; In 1,4-dioxane; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

2-((1R,2S,3R,4R)-4-(((tert-butyldimethylsilyl)oxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-2-methoxycyclopentyl)isoindoline-1,3-dione (1596364-67-8) → (1S,2R,3S,4R)-methyl 4-((5-(benzo[d]thiazol-2-yl)-2-((2,6-dimethylpyridin-4-yl)amino)pyrimidin-4-yl)amino)-2-((tert-butyldiphenylsilyl)oxy)-3-methoxycyclopentanecarboxylate (1596364-75-8)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridinium p-toluenesulfonate / ethanol / 18 h / 50 °C

2: sodium periodate; ruthenium(III) trichloride hydrate / water; tetrachloromethane; acetonitrile / 1 h

3: diazomethyl-trimethyl-silane / toluene / 0 - 20 °C

4: hydrazine / ethanol; diethyl ether / 18 h / 20 °C

5: triethylamine / ethanol / 18 h / 80 °C

6: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

7: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C

8: ammonium hydroxide / 1,4-dioxane; water / 1 h / 80 °C / Sealed tube

9: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium phenoxide / 1,4-dioxane / 18 h / 100 °C

With ammonium hydroxide; sodium periodate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ruthenium(III) trichloride hydrate; sodium phenoxide; pyridinium p-toluenesulfonate; caesium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; hydrazine; diazomethyl-trimethyl-silane; In 1,4-dioxane; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

2-(1R,2S,3R,4R)-3-hydroxy-4-(hydroxymethyl)-2-methoxycyclopentylisoindoline-1,3-dione

2-((6aR,8R,9S,9aR)-2,2,4,4-tetraisopropyl-9-methoxyhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-8-yl)isoindoline-1,3-dione

2-((1R,2S,3R,4R)-4-(((tert-butyldimethylsilyl)oxy)methyl)-3-hydroxy-2-methoxycyclopentyl)isoindoline-1,3-dione

2-((1R,2S,3R,4R)-4-(((tert-butyldimethylsilyl)oxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-2-methoxycyclopentyl)isoindoline-1,3-dione