(3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole

Base Information

• Chemical Name: (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole
• CAS No.: 2214207-73-3
• Molecular Formula: C₂₂H₂₈O₂P₂
• Molecular Weight: 386.411

Synonyms:

Chemical Property of (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole

Chemical Property:

• Boiling Point: 528.0±50.0 °C(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

(3R,3'R)-3,3'-Di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole, min. 97% (99% ee) (3R,3'R)-BABIBOP ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole

There total 9 articles about (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole 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: 87.0%

(3R,3'R)-3,3'-di-tert-butyl-2H,2'H-[4,4'-bibenzo[d][1,3]oxaphosphole] 3,3'-dioxide → (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole (2214207-73-3)

Guidance literature:

With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane; In tetrahydrofuran; at 65 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00139

Reference yield:

(R)-3-(tert-butyl)-3-oxido-2H-benzo[d][1,3]oxaphosphol-4-yl trifluoromethanesulfonate (1202032-99-2) → (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole (2214207-73-3)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium bromide; 1,1'-bis(di-tertbutylphosphino)ferrocene / N,N-dimethyl acetamide / 140 °C / Inert atmosphere

2: 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate / tetrahydrofuran / 2 h / 65 °C / Inert atmosphere

With titanium(IV) isopropylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,1'-bis(di-tertbutylphosphino)ferrocene; 1,1,3,3-Tetramethyldisiloxane; potassium bromide; zinc; In tetrahydrofuran; N,N-dimethyl acetamide;

DOI:10.1021/acs.orglett.8b00139

Reference yield:

tert-butyl(2,6-dimethoxyphenyl)phosphine oxide → (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole (2214207-73-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydroxide / 0.5 h / 65 - 75 °C

2.1: hydrogen iodide / 24 h / 92 - 100 °C

3.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / -5 - 25 °C

3.2: 1 h / 60 °C

4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 60 °C

5.1: sodium hydroxide; water / methanol / 2 h / 65 °C

6.1: triethylamine / dichloromethane / 1 h / 20 °C

7.1: potassium bromide; zinc; XPhos / 1.5 h / 140 - 150 °C / Inert atmosphere

8.1: titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane / tetrahydrofuran / 2 h / 65 °C / Inert atmosphere

With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane; water; hydrogen iodide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium bromide; sodium hydroxide; zinc; XPhos; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

upstream raw materials:

(R)-3-(tert-butyl)-3-oxido-2H-benzo[d][1,3]oxaphosphol-4-yl trifluoromethanesulfonate

racemic 3-tert-butyl-2,3-dihydrobenzo[d][1,3]oxaphosphol-4-ol oxide

(R)-3-(tert-butyl)-4-hydroxy-2H-benzo[ d][1,3]oxaphosphole 3-oxide

(R)-3-(tert-butyl)-3-oxido-2H-benzo[d][1,3]oxaphosphol-4-yl ((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) carbonate

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