(S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Base Information

• Chemical Name: (S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester
• CAS No.: 89495-30-7
• Molecular Formula: C₃₅H₄₄O₁₀
• Molecular Weight: 624.728

Synonyms:(S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property of (S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

There total 19 articles about (S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl 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:

2-chloro-5-methoxy-6-(2-propenyl)naphthoquinone (89414-71-1) → (S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester (89495-30-7)

Guidance literature:

Multi-step reaction with 7 steps

1: PdCl₂-bis(acetonitrile) / CH₂Cl₂ / 12 h / Heating

3: 1.) O₃, 2.) Me₂S

4: 92 percent / tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium / CHCl₃ / 65 °C

5: 1.) BH₃*Me₂S, 2.) H₂O₂, NaOH / 1.) THF

6: BBr₃ / CH₂Cl₂

With sodium hydroxide; dimethylsulfide; dimethylsulfide borane complex; dihydrogen peroxide; boron tribromide; ozone; dichloro bis(acetonitrile) palladium(II); tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium; In dichloromethane; chloroform;

DOI:10.1021/ja00320a049

Reference yield:

1,5-dimethoxy-2-formyl-6-(2-oxopropyl)-9,10-anthraquinone (89414-68-6) → (S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester (89495-30-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium / CHCl₃ / 65 °C

2: 1.) BH₃*Me₂S, 2.) H₂O₂, NaOH / 1.) THF

3: BBr₃ / CH₂Cl₂

With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide; boron tribromide; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium; In dichloromethane; chloroform;

DOI:10.1021/ja00320a049

Reference yield:

2-Chloro-5-methoxy-6-((Z)-propenyl)-[1,4]naphthoquinone (89414-72-2) → (S)-4-[6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-3-hydroxy-3-methyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester (89495-30-7)

Guidance literature:

Multi-step reaction with 6 steps

2: 1.) O₃, 2.) Me₂S

3: 92 percent / tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium / CHCl₃ / 65 °C

4: 1.) BH₃*Me₂S, 2.) H₂O₂, NaOH / 1.) THF

5: BBr₃ / CH₂Cl₂

With sodium hydroxide; dimethylsulfide; dimethylsulfide borane complex; dihydrogen peroxide; boron tribromide; ozone; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium; In dichloromethane; chloroform;

DOI:10.1021/ja00320a049

upstream raw materials:

1,5-Dihydroxy-2-((2R,4R,5R,6R)-5-hydroxy-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl)-6-(2-oxo-propyl)-anthraquinone

2-chloro-5-methoxy-6-(2-propenyl)naphthoquinone

1,5-dimethoxy-2-formyl-6-(2-oxopropyl)-9,10-anthraquinone

1,5-dimethoxy-2-(tetrahydro-5-hydroxy-6-methyl-4-((triethylsilyl)oxy)-2H-pyran-2-yl)-6-(2-oxopropyl)-9,10-anthraquinone

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