Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

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Chemical Name:Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester
CAS No.:436153-50-3
Molecular Formula:C₃₅H₄₉O₉PSi
Molecular Weight:672.828
Hs Code.:

Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

Synonyms:Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

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Chemical Property of Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

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Technology Process of Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

There total 51 articles about Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-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:

: 436153-62-7
(5R,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-6-methoxymethoxy-6,10-dimethyl-undec-9-en-5-ol

: 436153-50-3
Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

Guidance literature:: Multi-step reaction with 25 steps

1.1: 7.93 g / potassium t-butoxide / tetrahydrofuran / 0 - 20 °C

2.1: N-methylmorpholine-N-oxide; aq. OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 72 h / 20 °C

3.1: aq. NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

4.1: 5.67 g / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: potassium t-butoxide / tetrahydrofuran / 0 - 20 °C

6.1: 5.23 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

7.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.5 h / 0 °C

8.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

9.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

9.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating

10.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C

11.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

11.2: 15.73 g / PdCl₂(dppf)*CH₂Cl₂; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C

12.1: BH₃*SMe₂ / tetrahydrofuran / 4.5 h / 20 °C

12.2: 33 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2.5 h / 20 °C

13.1: 85 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; 4A molecular sieves / acetonitrile / 2.5 h / 20 °C

14.1: 51 percent / DBU / toluene / 12 h / 110 °C

15.1: 74 percent / Zn(OTf)2 / CH₂Cl₂ / 15.5 h / 20 °C

16.1: camphorsulphonic acid / CH₂Cl₂ / 4.5 h / 20 °C

17.1: AIBN; Ph₃SnH / toluene / 3.5 h / 100 °C

18.1: 4.37 g / DIBALH / CH₂Cl₂; hexane / -78 - 0 °C

19.1: 89 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 20 °C

20.1: AIBN; n-Bu₃SnH / toluene / 0.83 h / 100 °C

21.1: 0.931 g / DDQ / CH₂Cl₂; aq. phosphate buffer / 2.5 h / 20 °C / pH 7

22.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

23.1: H₂ / Pd(OH)2/C / ethyl acetate; methanol / 20 h / 20 °C

24.1: 679.1 mg / 2,2,6,6-tetramethylpiperidinyloxy; iodobenzenediacetate / CH₂Cl₂ / 4.5 h / 20 °C

25.1: KHMDS; hexamethylphosphoroamide / tetrahydrofuran; toluene / 0.75 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; triphenylstannane; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; benzene; 7.1: Swern oxidation / 11.2: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ja042686r

Reference yield:

: (4S,5R)-5-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-4-methyl-nonanal

: 436153-50-3
Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

Guidance literature:: Multi-step reaction with 22 steps

1.1: 5.67 g / NaBH₄ / methanol / 0.5 h / 0 °C

2.1: potassium t-butoxide / tetrahydrofuran / 0 - 20 °C

3.1: 5.23 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

4.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.5 h / 0 °C

5.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

6.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

6.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating

7.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C

8.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

8.2: 15.73 g / PdCl₂(dppf)*CH₂Cl₂; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C

9.1: BH₃*SMe₂ / tetrahydrofuran / 4.5 h / 20 °C

9.2: 33 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2.5 h / 20 °C

10.1: 85 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; 4A molecular sieves / acetonitrile / 2.5 h / 20 °C

11.1: 51 percent / DBU / toluene / 12 h / 110 °C

12.1: 74 percent / Zn(OTf)2 / CH₂Cl₂ / 15.5 h / 20 °C

13.1: camphorsulphonic acid / CH₂Cl₂ / 4.5 h / 20 °C

14.1: AIBN; Ph₃SnH / toluene / 3.5 h / 100 °C

15.1: 4.37 g / DIBALH / CH₂Cl₂; hexane / -78 - 0 °C

16.1: 89 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 20 °C

17.1: AIBN; n-Bu₃SnH / toluene / 0.83 h / 100 °C

18.1: 0.931 g / DDQ / CH₂Cl₂; aq. phosphate buffer / 2.5 h / 20 °C / pH 7

19.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

20.1: H₂ / Pd(OH)2/C / ethyl acetate; methanol / 20 h / 20 °C

21.1: 679.1 mg / 2,2,6,6-tetramethylpiperidinyloxy; iodobenzenediacetate / CH₂Cl₂ / 4.5 h / 20 °C

22.1: KHMDS; hexamethylphosphoroamide / tetrahydrofuran; toluene / 0.75 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; triphenylstannane; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; benzene; 4.1: Swern oxidation / 8.2: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ja042686r

Reference yield:

: (5R,6S)-5,9-Bis-benzyloxy-6-methoxymethoxy-6-methyl-nonanal

: 436153-50-3
Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

2.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating

3.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C

4.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

4.2: 15.73 g / PdCl₂(dppf)*CH₂Cl₂; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C

5.1: BH₃*SMe₂ / tetrahydrofuran / 4.5 h / 20 °C

5.2: 33 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2.5 h / 20 °C

6.1: 85 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; 4A molecular sieves / acetonitrile / 2.5 h / 20 °C

7.1: 51 percent / DBU / toluene / 12 h / 110 °C

8.1: 74 percent / Zn(OTf)2 / CH₂Cl₂ / 15.5 h / 20 °C

9.1: camphorsulphonic acid / CH₂Cl₂ / 4.5 h / 20 °C

10.1: AIBN; Ph₃SnH / toluene / 3.5 h / 100 °C

11.1: 4.37 g / DIBALH / CH₂Cl₂; hexane / -78 - 0 °C

12.1: 89 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 20 °C

13.1: AIBN; n-Bu₃SnH / toluene / 0.83 h / 100 °C

14.1: 0.931 g / DDQ / CH₂Cl₂; aq. phosphate buffer / 2.5 h / 20 °C / pH 7

15.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

16.1: H₂ / Pd(OH)2/C / ethyl acetate; methanol / 20 h / 20 °C

17.1: 679.1 mg / 2,2,6,6-tetramethylpiperidinyloxy; iodobenzenediacetate / CH₂Cl₂ / 4.5 h / 20 °C

18.1: KHMDS; hexamethylphosphoroamide / tetrahydrofuran; toluene / 0.75 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; triphenylstannane; hydrogen; iodine; tri-n-butyl-tin hydride; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; benzene; 4.2: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ja042686r