(4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide

Base Information

• Chemical Name: (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide
• CAS No.: 1268519-05-6
• Molecular Formula: C₁₄H₈Br₄O₄S
• Molecular Weight: 591.897
• Mol file: 1268519-05-6.mol

Synonyms:(4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide

Chemical Property of (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide

There total 7 articles about (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide 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: 93.0%

(1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol (1268519-04-5) → (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide (1268519-05-6)

Guidance literature:

(1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol; With thionyl chloride; In tetrachloromethane; for 4h; Inert atmosphere; Reflux;

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.10.027

Reference yield:

3,5-dibromobenzaldehyde (56990-02-4) → (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide (1268519-05-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.1: methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tetrahydrofuran; water; tert-butyl alcohol / 120 h / 0 °C / Inert atmosphere

3.1: thionyl chloride / tetrachloromethane / 4 h / Inert atmosphere; Reflux

3.2: 3 h / 20 °C / Inert atmosphere

With thionyl chloride; methanesulfonamide; potassium tert-butylate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; In tetrahydrofuran; tetrachloromethane; water; tert-butyl alcohol; 1.1: Wittig reaction / 2.1: Sharpless dihydroxylation;

DOI:10.1016/j.tetasy.2010.10.027

Reference yield:

(E)-1,2-bis(3,5-dibromophenyl)ethene → (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide (1268519-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tetrahydrofuran; water; tert-butyl alcohol / 120 h / 0 °C / Inert atmosphere

2.1: thionyl chloride / tetrachloromethane / 4 h / Inert atmosphere; Reflux

2.2: 3 h / 20 °C / Inert atmosphere

With thionyl chloride; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; In tetrahydrofuran; tetrachloromethane; water; tert-butyl alcohol; 1.1: Sharpless dihydroxylation;

DOI:10.1016/j.tetasy.2010.10.027

upstream raw materials:

(1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol

3,5-dibromotoluene

3,5-dibromobenzaldehyde

3,5-dibromobenzyl bromide

Downstream raw materials:

(2R,3R)-1-(ethoxycarbonyl)-2,3-bis(3',5'-dibromophenyl)cyclopropane-1-carboxylic acid

(2R,3R)-2,3-bis(3',5'-dibromophenyl)cyclopropane-1,1-dimethanol

(2R,3R)-2,3-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol

(2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane