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

Base Information

• Chemical Name: (R)-3-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-2-hydroxy-2-methylpropyl 4-methylbenzenesulfonate
• CAS No.: 1349697-70-6
• Molecular Formula: C₃₉H₃₄O₈S
• Molecular Weight: 662.76
• Mol file: 1349697-70-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (R)-3-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-2-hydroxy-2-methylpropyl 4-methylbenzenesulfonate 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: 91.0%

(R)-1,5-bis(benzyloxy)-2-(2,3-dihydroxy-2-methylpropyl)anthracene-9,10-dione (1349697-69-3) + p-toluenesulfonyl chloride (98-59-9) → (R)-3-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-2-hydroxy-2-methylpropyl 4-methylbenzenesulfonate (1349697-70-6)

Guidance literature:

With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol203041b

Reference yield:

1,5-bis(benzyloxy)-2-(2-methylallyl)anthracene-9,10-dione (1349697-67-1) → (R)-3-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-2-hydroxy-2-methylpropyl 4-methylbenzenesulfonate (1349697-70-6)

Guidance literature:

Multi-step reaction with 2 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

With osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether; di(n-butyl)tin oxide; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol; 1: Sharpless dihydroxylation;

DOI:10.1021/ol203041b

Reference yield:

1,5-dihydroxyanthraquinone (117-12-4) → (R)-3-(1,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracen-2-yl)-2-hydroxy-2-methylpropyl 4-methylbenzenesulfonate (1349697-70-6)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 7 h / 75 °C / Inert atmosphere

2: sodium dithionite / water; N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere

3: potassium carbonate / acetone / Reflux

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

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

With osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether; sodium dithionite; di(n-butyl)tin oxide; potassium carbonate; triethylamine; potassium iodide; potassium hexacyanoferrate(III); In dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 2: Claisen rearrangement / 4: Sharpless dihydroxylation;

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

p-toluenesulfonyl chloride

1,5-dihydroxyanthraquinone

Downstream raw materials:

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

(R)-1,5-bis(benzyloxy)-2-((2-methyl-4-oxooxetan-2-yl)methyl)anthracene-9,10-dione

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

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