(4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine>

Base Information

• Chemical Name: (4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine>
• CAS No.: 140189-33-9
• Molecular Formula: C₅₄H₇₈N₂O₄P₂
• Molecular Weight: 881.172
• Mol file: 140189-33-9.mol

Synonyms:(4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine>

Chemical Property of (4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine>

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine>

There total 8 articles about (4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine> 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: 44.0%

3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol (6390-69-8) + (4S,5R)-2-chloro-4-methyl-3-(2-methylpropyl)-5-phenyl-1,3,2-oxazaphospholidine (140189-32-8) → (4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine> (140189-33-9)

Guidance literature:

3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol; With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at 30 ℃; for 1h; Inert atmosphere; Schlenk technique;

(4S,5R)-2-chloro-4-methyl-3-(2-methylpropyl)-5-phenyl-1,3,2-oxazaphospholidine; In tetrahydrofuran; diethyl ether; hexane; at 20 ℃; for 40h; Inert atmosphere; Schlenk technique;

DOI:10.1002/hlca.19910740605

Reference yield:

(1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) → (4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine> (140189-33-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene / 0.25 h / Inert atmosphere; Schlenk technique; Reflux

2.1: sodium tetrahydroborate / methanol; water / 1.25 h / 20 °C / Inert atmosphere; Schlenk technique

3.1: phosphorus trichloride; triethylamine / dichloromethane / 1 h / Inert atmosphere; Schlenk technique; Reflux

4.1: n-butyllithium / diethyl ether; hexane; tetrahydrofuran / 1 h / 30 °C / Inert atmosphere; Schlenk technique

4.2: 40 h / 20 °C / Inert atmosphere; Schlenk technique

5.1: n-butyllithium / diethyl ether; hexane; tetrahydrofuran / 1 h / 30 °C / Inert atmosphere; Schlenk technique

5.2: 40 h / 20 °C / Inert atmosphere; Schlenk technique

With sodium tetrahydroborate; n-butyllithium; triethylamine; phosphorus trichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene;

DOI:10.1002/hlca.19910740605

Reference yield:

(1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8) → (4S,4'S,5R,5'R)-4,4'-dimethyl-3,3'-bis(2-methylpropyl)-5,5'-diphenyl-2,2'-<<3,3',5,5'-tetrakis(1,1-dimethylethyl)-1,1'-biphenyl-2,2'-diyl>bis(oxy)>bis<1,3,2-oxazaphospholidine> (140189-33-9)

Guidance literature:

Multi-step reaction with 4 steps

1: benzene / 0.25 h / Heating

2: NaBH₄ / methanol; H₂O / 2 h / Ambient temperature

3: 86 percent / 1) PCl₃ 2) NEt₃ / CH₂Cl₂ / 1 h / Heating

4: 1) BuLi / hexane, Et₂O

With sodium tetrahydroborate; n-butyllithium; triethylamine; phosphorus trichloride; In methanol; dichloromethane; water; benzene;

DOI:10.1002/hlca.19910740605

upstream raw materials:

3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol

(4S,5R)-2-chloro-4-methyl-3-(2-methylpropyl)-5-phenyl-1,3,2-oxazaphospholidine

(1R,2S)-norephedrine

(-)-(1R,2S)-2-<(2-methylpropyl)amino>-1-phenylpropanol