(3aR,8aR)-(-)-4,4,8,8-Tetrakis (3,5-di-i-propylphenyl)tetrahydro-2,2-diMethyl-6-phenyl-1,3-dioxolo[4,5-e]dioxaphosphepin

Base Information

• Chemical Name: (3aR,8aR)-(-)-4,4,8,8-Tetrakis (3,5-di-i-propylphenyl)tetrahydro-2,2-diMethyl-6-phenyl-1,3-dioxolo[4,5-e]dioxaphosphepin
• CAS No.: 1361146-90-8
• Molecular Formula: C61H82O4P
• Molecular Weight: 909.285
• Mol file: 1361146-90-8.mol

Synonyms:(3aR,8aR)-(-)-4,4,8,8-Tetrakis (3,5-di-i-propylphenyl)tetrahydro-2,2-diMethyl-6-phenyl-1,3-dioxolo[4,5-e]dioxaphosphepin;(3aR,8aR)-(-)-4,4,8,8-Tetrakis(3,5-di-i-propylphenyl)tetrahydro-2,2-dimethyl-6-phenyl-1,3-dioxolo[4,5-e]dioxaphosphepine;(3aR,8aR)-4,4,8,8-Tetrakis[3,5-bis(1-methylethyl)phenyl]tetrahydro-2,2-dimethyl-6-phenyl-1,3-dioxolo[4,5-e][1,3,2]dioxaphosphepin

Chemical Property of (3aR,8aR)-(-)-4,4,8,8-Tetrakis (3,5-di-i-propylphenyl)tetrahydro-2,2-diMethyl-6-phenyl-1,3-dioxolo[4,5-e]dioxaphosphepin

Chemical Property:

• Boiling Point: 764.8±60.0 °C(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

(3aR,8aR)-(-)-4,4,8,8-Tetrakis(3,5-di-i-propylphenyl)tetrahydro-2,2-dimethyl-6-phenyl-1,3-dioxolo[4,5-e]dioxaphosphepin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,8aR)-(-)-4,4,8,8-Tetrakis (3,5-di-i-propylphenyl)tetrahydro-2,2-diMethyl-6-phenyl-1,3-dioxolo[4,5-e]dioxaphosphepin

There total 5 articles about (3aR,8aR)-(-)-4,4,8,8-Tetrakis (3,5-di-i-propylphenyl)tetrahydro-2,2-diMethyl-6-phenyl-1,3-dioxolo[4,5-e]dioxaphosphepin 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: 92.0%

((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(bis(3,5-diisopropylphenyl)methanol) (1361146-89-5) + Dichlorophenylphosphine (644-97-3) → (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine (1361146-90-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ja4041016

Reference yield:

4-bromo-2,6-diisopropylaniline (80058-84-0) → (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine (1361146-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hypophosphorous acid; sodium nitrite; hydrogenchloride / 4 - 20 °C / Inert atmosphere

2.1: magnesium; iodine / tetrahydrofuran / 3 h / 80 °C / Inert atmosphere

2.2: 12 h / 0 - 80 °C / Inert atmosphere

3.1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; iodine; hypophosphorous acid; magnesium; triethylamine; sodium nitrite; In tetrahydrofuran;

DOI:10.1021/ja4041016

Reference yield:

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) + 1-bromo-3,5-bis(propan-2-yl)benzene (23058-81-3) → (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine (1361146-90-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium / tetrahydrofuran / 0.25 h / Reflux

1.2: Reflux

2.1: triethylamine / tetrahydrofuran / 2 h / 25 °C

With magnesium; triethylamine; In tetrahydrofuran;

DOI:10.1021/acs.orglett.9b00090

upstream raw materials:

1-bromo-3,5-bis(propan-2-yl)benzene

2,6-diisopropylbenzenamine

4-bromo-2,6-diisopropylaniline

((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(bis(3,5-diisopropylphenyl)methanol)

Refernces

• 1、 Dailler, David,Rocaboy, Ronan,Baudoin, Olivier. "Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)?H Carbamoylation". supporting information. p. 7218 - 7222. Retrieved 2017/06/13.
• 2、 Coombs, John R.,Haeffner, Fredrik,Kliman, Laura T.,Morken, James P.. "Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes". . p. 11222 - 11231. Retrieved 2013/08/23.