Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester

Base Information

• Chemical Name: Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester
• CAS No.: 125250-90-0
• Molecular Formula: C₂₆H₃₃O₄P
• Molecular Weight: 440.519
• Mol file: 125250-90-0.mol

Synonyms:Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester

Chemical Property of Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester

There total 12 articles about Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester 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: 80.0%

(2R*,3R*)-2,3-diphenylspiro<4.5>decan-6-one (125250-89-7) + diethyl chlorophosphate (814-49-3) → Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester (125250-90-0)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; -78 deg C to room temperature;

DOI:10.1021/jo00294a016

Reference yield:

ethyl 3-phenyl-2-propenoate (103-36-6) → Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester (125250-90-0)

Guidance literature:

Multi-step reaction with 12 steps

1: sodium / diethyl ether / 3 h / Heating

2: 20percent HBr / aq. ethanol / Heating

3: 92 percent / Zn dust, TiCl₄ / tetrahydrofuran / 2.5 h / Ambient temperature

4: 1.) BH₃*THF, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C to room temperature, 2.) room temperature, 1 h

5: 95 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.33 h / -60 °C

6: Br₂, sodium bicarbonate buffer / H₂O

7: 1.) n-BuLi, diisopropylamine / 1.) THF, -60 deg C, 30 min, 2.) -60 to -15 deg C

8: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran

9: 1.) oxalyl chloride, DMSO, 2.) Br₂, NaHCO₃ buffer / 1.) CH₂Cl₂, 2.) H₂O

10: n-BuLi, diisopropylamine / tetrahydrofuran / -78 deg C to room temperature

11: NaOH / aq. ethanol / Heating

12: 80 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 deg C to room temperature

With sodium hydroxide; n-butyllithium; borane-THF; oxalyl dichloride; NaHCO₃ buffer; sodium bicarbonate buffer; tetrabutyl ammonium fluoride; hydrogen bromide; dihydrogen peroxide; bromine; sodium; titanium tetrachloride; dimethyl sulfoxide; diisopropylamine; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jo00294a016

Reference yield:

2,3-Diphenyl-5-oxo-cyclopentancarbonsaeureethylester (7356-94-7) → Phosphoric acid (2S,3S)-2,3-diphenyl-spiro[4.5]dec-6-en-6-yl ester diethyl ester (125250-90-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 20percent HBr / aq. ethanol / Heating

2: 92 percent / Zn dust, TiCl₄ / tetrahydrofuran / 2.5 h / Ambient temperature

3: 1.) BH₃*THF, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C to room temperature, 2.) room temperature, 1 h

4: 95 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.33 h / -60 °C

5: Br₂, sodium bicarbonate buffer / H₂O

6: 1.) n-BuLi, diisopropylamine / 1.) THF, -60 deg C, 30 min, 2.) -60 to -15 deg C

7: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran

8: 1.) oxalyl chloride, DMSO, 2.) Br₂, NaHCO₃ buffer / 1.) CH₂Cl₂, 2.) H₂O

9: n-BuLi, diisopropylamine / tetrahydrofuran / -78 deg C to room temperature

10: NaOH / aq. ethanol / Heating

11: 80 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 deg C to room temperature

With sodium hydroxide; n-butyllithium; borane-THF; oxalyl dichloride; NaHCO₃ buffer; sodium bicarbonate buffer; tetrabutyl ammonium fluoride; hydrogen bromide; dihydrogen peroxide; bromine; titanium tetrachloride; dimethyl sulfoxide; diisopropylamine; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1021/jo00294a016

upstream raw materials:

(2R*,3R*)-2,3-diphenylspiro<4.5>decan-6-one

diethyl chlorophosphate

ethyl 3-phenyl-2-propenoate

2,3-Diphenyl-5-oxo-cyclopentancarbonsaeureethylester

Downstream raw materials:

spiroheptane-2,1'-3,4-diphenylcyclopentane>

spiroheptane-2,1'-3,4-diphenylcyclopentane>

(2R*,3R*)-2,3-diphenylspiro<4.5>dec-6-ene

Refernces