Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester

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Chemical Name:Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester
CAS No.:908865-85-0
Molecular Formula:C₄₂H₅₁O₇PSi
Molecular Weight:726.922
Hs Code.:

Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester

Synonyms:Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester

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Chemical Property of Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester

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Technology Process of Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester

There total 23 articles about Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl 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: 96.0%

: 908866-05-7
(2S,3S,4aS,9aR)-2-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-6-one

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 908865-85-0
Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h;
DOI:10.1021/ja062524q

Reference yield:

: 908865-90-7
(2S,3S)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexane-1,3-diol

: 908865-85-0
Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: CSA / CH₂Cl₂ / 1 h / 20 °C

2.1: 5.99 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - -40 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

4.1: 675.3 mg / dimethylsulfoxide / 2.5 h / 60 °C

5.1: 90 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

6.1: 97 percent / toluene / 0.5 h / 100 °C

7.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

8.1: 88 percent / (+)-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 1.17 h / -40 °C

9.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

10.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

10.2: 7.71 g / tetrahydrofuran / 0.5 h / 0 °C

11.1: DDQ; water / CH₂Cl₂ / 7 h / 0 - 20 °C

12.1: 10.37 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

13.1: (Sia)2BH / tetrahydrofuran / 1.5 h / 0 °C

13.2: 92 percent / aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 0 - 20 °C

14.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.83 h / 0 °C

15.1: 3.87 g / toluene / 19 h / 45 - 60 °C

16.1: 95 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

17.1: 90 percent / H₂ / Pd(OH)2/C / methanol; tetrahydrofuran / 2.5 h / 20 °C

18.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

18.2: 98 percent / DMAP / tetrahydrofuran; toluene / 3.5 h / 110 °C

19.1: 96 percent / KHMDS / hexamethylphosphoric acid triamide; toluene / 1 h / -78 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; (Sia)2BH; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; water; hydrogen; sodium hexamethyldisilazane; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; 4 A molecular sieve; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; decane; hexane; dichloromethane; dimethyl sulfoxide; toluene; 6.1: Wittig reaction / 8.1: Sharpless epoxidation / 10.2: Wittig olefination / 15.1: Wittig reaction / 18.2: Yamaguchi lactonization;
DOI:10.1021/ja066772y

Reference yield:

: 924656-30-4
(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-2-vinyl-tetrahydro-pyran-3-ol

: 908865-85-0
Phosphoric acid (2S,3S,4aS,9aR)-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-3,4,4a,8,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl ester diphenyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 10.37 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: (Sia)2BH / tetrahydrofuran / 1.5 h / 0 °C

2.2: 92 percent / aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 0 - 20 °C

3.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.83 h / 0 °C

4.1: 3.87 g / toluene / 19 h / 45 - 60 °C

5.1: 95 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

6.1: 90 percent / H₂ / Pd(OH)2/C / methanol; tetrahydrofuran / 2.5 h / 20 °C

7.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

7.2: 98 percent / DMAP / tetrahydrofuran; toluene / 3.5 h / 110 °C

8.1: 96 percent / KHMDS / hexamethylphosphoric acid triamide; toluene / 1 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; pyridine-SO₃ complex; (Sia)2BH; 2,4,6-trichlorobenzoyl chloride; hydrogen; potassium hexamethylsilazane; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; dimethyl sulfoxide; toluene; 4.1: Wittig reaction / 7.2: Yamaguchi lactonization;
DOI:10.1021/ja066772y