(4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one

Base Information

Chemical Name:(4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one
CAS No.:204395-33-5
Molecular Formula:C₃₈H₆₀O₆Si₂
Molecular Weight:669.062
Hs Code.:

Synonyms:(4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one

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Chemical Property of (4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one

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Technology Process of (4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one

There total 16 articles about (4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one 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: 82.0%

: 204395-32-4
(3S,4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-methyl-7-triethylsilanyloxy-nonane-3,4-diol

: 204395-33-5
(4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one

Guidance literature:: With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; for 2h; Ambient temperature;
DOI:10.1055/s-1998-1648

Reference yield:

: 35334-60-2
(E)-6-acetoxy-4-methyl-4-hexenal

: 204395-33-5
(4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one

Guidance literature:: Multi-step reaction with 15 steps

1: toluene / 16 h / Ambient temperature

2: Na / methanol / 5 h / 0 °C

3: MsCl, Et₃N, LiCl / dimethylformamide; CH₂Cl₂ / 6 h / -20 - 0 °C

4: Et₄NF, 4 Angstroem molecular sieves, Bu₄NI / dimethylformamide / 1.) r.t., 15 min, 2.) r.t., 3 h

5: aq. NaOH / 2-methyl-propan-2-ol / 16 h

6: KHSO₄ / toluene / 5 h / 60 °C

7: pyridinium p-toluenesulfonate / methanol / 24 h / Ambient temperature

8: toluene / 1 h

9: DIBAL-H / tetrahydrofuran; hexane / 3 h / -78 - -60 °C

10: 89 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / -20 °C

11: 97 percent / Red-Al / tetrahydrofuran / 16 h / -20 - 0 °C

12: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

13: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

14: (DHQ)2PHAL, aq. OsO₄, K₃Fe(CN)6, MeSO₂NH₂, K₂CO₃ / 2-methyl-propan-2-ol / 5.5 h / 0 - 20 °C

15: 82 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide / 2 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium hydroxide; potassium hydrogensulfate; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; pyridine-SO₃ complex; methanesulfonamide; 4 A molecular sieve; sodium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; tetraethylammonium fluoride; potassium carbonate; methanesulfonyl chloride; (-)-diethyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium chloride; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1055/s-1998-1648

Reference yield:

: 204395-25-5
(2E,6E)-8-Chloro-6-methyl-octa-2,6-dienoic acid tert-butyl ester

: 204395-33-5
(4S,7R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-(1S,5S)-6,8-dioxa-bicyclo[3.2.1]oct-5-yl-4-hydroxy-4-methyl-7-triethylsilanyloxy-nonan-3-one

Guidance literature:: Multi-step reaction with 12 steps

1: Et₄NF, 4 Angstroem molecular sieves, Bu₄NI / dimethylformamide / 1.) r.t., 15 min, 2.) r.t., 3 h

2: aq. NaOH / 2-methyl-propan-2-ol / 16 h

3: KHSO₄ / toluene / 5 h / 60 °C

4: pyridinium p-toluenesulfonate / methanol / 24 h / Ambient temperature

5: toluene / 1 h

6: DIBAL-H / tetrahydrofuran; hexane / 3 h / -78 - -60 °C

7: 89 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / -20 °C

8: 97 percent / Red-Al / tetrahydrofuran / 16 h / -20 - 0 °C

9: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

10: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

11: (DHQ)2PHAL, aq. OsO₄, K₃Fe(CN)6, MeSO₂NH₂, K₂CO₃ / 2-methyl-propan-2-ol / 5.5 h / 0 - 20 °C

12: 82 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide / 2 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium hydroxide; potassium hydrogensulfate; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; pyridine-SO₃ complex; methanesulfonamide; 4 A molecular sieve; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; tetraethylammonium fluoride; potassium carbonate; (-)-diethyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1055/s-1998-1648