(4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester

Base Information

• Chemical Name: (4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester
• CAS No.: 753497-76-6
• Molecular Formula: C₃₀H₃₉BrO₇
• Molecular Weight: 591.539

Synonyms:(4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester

Chemical Property of (4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester

Chemical Property:

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Technology Process of (4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester

There total 4 articles about (4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric 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: 61.0%

4-((4S,5R)-5-{[(4R,5R)-8-Bromo-2,2-dimethyl-7-oxo-4-(4-phenyl-butyl)-1,3-dioxa-spiro[4.4]non-8-en-6-yl]-hydroxy-methyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester (753497-75-5) → (4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(E)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester (753497-77-7) + (4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester (753497-76-6)

Guidance literature:

With pyridine; dmap; acetic anhydride; at 60 ℃; for 4h;

DOI:10.1039/b404016c

Reference yield:

methyl 4-(5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)butanoate (102354-82-5) → (4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester (753497-76-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

1.2: 41.6 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 20 percent / Ac₂O; 4-DMAP; pyridine / 4 h / 60 °C

With pyridine; dmap; acetic anhydride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1039/b404016c

Reference yield:

2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one → (4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(Z)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester (753497-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 300 mg / Br₂ / CH₂Cl₂ / 0.4 h

2.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

2.2: 41.6 percent / tetrahydrofuran / 0.5 h / -78 °C

3.1: 20 percent / Ac₂O; 4-DMAP; pyridine / 4 h / 60 °C

With pyridine; dmap; bromine; acetic anhydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b404016c

upstream raw materials:

4-((4S,5R)-5-{[(4R,5R)-8-Bromo-2,2-dimethyl-7-oxo-4-(4-phenyl-butyl)-1,3-dioxa-spiro[4.4]non-8-en-6-yl]-hydroxy-methyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester

methyl 4-(5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)butanoate

(5R)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

Downstream raw materials:

6(S)-{2(Z)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one

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