(R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid

Base Information

• Chemical Name: (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid
• CAS No.: 1349697-72-8
• Molecular Formula: C₃₃H₂₈O₇
• Molecular Weight: 536.581
• Mol file: 1349697-72-8.mol

Synonyms:(R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid

Chemical Property of (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid

There total 9 articles about (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid 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: 97.0%

(R)-1,5-bis(benzyloxy)-2-((2-methyl-4-oxooxetan-2-yl)methyl)anthracene-9,10-dione (1349697-71-7) → (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid (1349697-72-8)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol203041b

Reference yield:

1,5-bis(benzyloxy)-2-(2-methylallyl)anthracene-9,10-dione (1349697-67-1) → (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid (1349697-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1: osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 0 - 20 °C

2: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0 - 20 °C

3: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

4: bis(tetrahydrofuran)-meso-tetra(4-chlorophenyl)porphyrinato aluminum tetracarbonyl cobaltate / tetrahydrofuran / 20 h / 40 °C / 46544.6 Torr

5: water; sodium hydroxide / tetrahydrofuran / 1 h / 20 °C

With osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether; bis(tetrahydrofuran)-meso-tetra(4-chlorophenyl)porphyrinato aluminum tetracarbonyl cobaltate; water; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; sodium hydroxide; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; mineral oil; tert-butyl alcohol; 1: Sharpless dihydroxylation;

DOI:10.1021/ol203041b

Reference yield:

(R)-1,5-bis(benzyloxy)-2-(2,3-dihydroxy-2-methylpropyl)anthracene-9,10-dione (1349697-69-3) → (R)-4-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid (1349697-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0 - 20 °C

2: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

3: bis(tetrahydrofuran)-meso-tetra(4-chlorophenyl)porphyrinato aluminum tetracarbonyl cobaltate / tetrahydrofuran / 20 h / 40 °C / 46544.6 Torr

4: water; sodium hydroxide / tetrahydrofuran / 1 h / 20 °C

With bis(tetrahydrofuran)-meso-tetra(4-chlorophenyl)porphyrinato aluminum tetracarbonyl cobaltate; water; sodium hydride; di(n-butyl)tin oxide; triethylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; mineral oil;

DOI:10.1021/ol203041b

upstream raw materials:

1,5-bis(benzyloxy)-2-(2-methylallyl)anthracene-9,10-dione

(R)-1,5-bis(benzyloxy)-2-(2,3-dihydroxy-2-methylpropyl)anthracene-9,10-dione

(R)-3-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-2-hydroxy-2-methylpropyl 4-methylbenzenesulfonate

(R)-1,5-bis(benzyloxy)-2-((2-methyloxiran-2-yl)methyl)anthracene-9,10-dione