(5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-5-hydroxy-3-oxo-6-heptenoic acid ethyl ester

Base Information

• Chemical Name: (5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-5-hydroxy-3-oxo-6-heptenoic acid ethyl ester
• CAS No.: 901765-36-4
• Molecular Formula: C24H30 F N3 O6 S
• Molecular Weight: 507.583
• Mol file: 901765-36-4.mol

Synonyms:3-keto-5-hydroxy rosuvastatin ethyl ester;(5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-5-hydroxy-3-oxo-6-heptenoic acid ethyl ester;ethyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-oxo-(5S)-5-hydroxy-(6E)-heptenoate;(S,E)-Ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxy-3-oxohept-6-enoate;ethyl 6-(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[N-methyl-N-methylsulfonylamino]pyrimidin-5-yl]-(5S)-hydroxy-3-oxoheptenoate;ethyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-oxo-5(S)-hydroxy-6(E)-heptenoate;(S)-trans-ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxy-3-oxohept-6-enoate;3-keto-5-hydroxy-ethyl rosuvastatin;

Chemical Property of (5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-5-hydroxy-3-oxo-6-heptenoic acid ethyl ester

Chemical Property:

• PSA: 135.14000
• Density: 1.291
• LogP: 4.16920
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

3-KetorosuvastatinEthylEster(85%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 901765-36-4 is a reagent in production of rosuvastatin.

Technology Process of (5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-5-hydroxy-3-oxo-6-heptenoic acid ethyl ester

There total 5 articles about (5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-5-hydroxy-3-oxo-6-heptenoic acid ethyl 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: 100.0%

(E)-N-[4-(4-fluorophenyl)-6-isopropyl-5-(3-oxoprop-1-en-1-yl)pyrimidin-2-yl]-N-methyl methanesulfoneamide (890028-66-7) + 1-ethoxy-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene (89186-81-2) → (S,E)-ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxy-3-oxohept-6-enoate (901765-36-4)

Guidance literature:

(E)-N-[4-(4-fluorophenyl)-6-isopropyl-5-(3-oxoprop-1-en-1-yl)pyrimidin-2-yl]-N-methyl methanesulfoneamide; With titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; water; at 25 ℃; for 0.166667h; Inert atmosphere; Molecular sieve;

1-ethoxy-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene; In tetrahydrofuran; water; at 25 ℃; for 16h; Molecular sieve; Inert atmosphere;

With phosphoric acid; In tetrahydrofuran; water; for 3h; Reagent/catalyst; Solvent; Cooling with ice;

DOI:10.1016/j.tetlet.2016.02.037

Reference yield: 92.0%

(S)-trans-ethyl 3-ethoxy-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxyhept-2,6-dienoate (1030595-88-0) → (S,E)-ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxy-3-oxohept-6-enoate (901765-36-4)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 0 - 25 ℃; for 1.5h;

Reference yield: 66.0%

ethyl 6-(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[N-methyl-N-methylsulfonylamino]pyrimidin-5-yl]-(5S)-5-(t-butyldimethylsilyloxy)-3-oxoheptenoate (1045601-10-2) → (S,E)-ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxy-3-oxohept-6-enoate (901765-36-4)

Guidance literature:

ethyl 6-(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[N-methyl-N-methylsulfonylamino]pyrimidin-5-yl]-(5S)-5-(t-butyldimethylsilyloxy)-3-oxoheptenoate; With hydrogen fluoride; In water; acetonitrile; at 0 - 30 ℃; for 0.333333 - 2.25h;

With sodium hydrogencarbonate; In water; acetonitrile; Product distribution / selectivity;

upstream raw materials:

(E)-N-[4-(4-fluorophenyl)-6-isopropyl-5-(3-oxoprop-1-en-1-yl)pyrimidin-2-yl]-N-methyl methanesulfoneamide

(S)-trans-ethyl 3-ethoxy-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxyhept-2,6-dienoate

ethyl 6-(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[N-methyl-N-methylsulfonylamino]pyrimidin-5-yl]-(5S)-5-(t-butyldimethylsilyloxy)-3-oxoheptenoate

1-ethoxy-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene

Downstream raw materials:

ethyl (3R),(5S),(6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-3,5-dihydroxy-6-heptenoate

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