(S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Base Information

• Chemical Name: (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
• CAS No.: 143842-95-9
• Molecular Formula: C₅₅H₇₀O₆Si₂
• Molecular Weight: 883.328
• Mol file: 143842-95-9.mol

Synonyms:(S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Chemical Property of (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

There total 23 articles about (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl 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: 86.0%

(S)-2-Methyl-butyric acid (1S,3S,5S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-5-hydroxy-7-methyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester (143842-94-8) → (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (143842-95-9)

Guidance literature:

With methoxycarbonylsulfamoyl-triethylammmonium hydroxide; In benzene; at 80 ℃; for 0.25h;

DOI:10.1021/jo00052a029

Reference yield:

(1S,3R,7S,8S,8aR)-8-((E)-3-Methoxy-allyl)-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1,3-diol → (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (143842-95-9)

Guidance literature:

Multi-step reaction with 12 steps

1: pyridine, 4-(N,N-dimethylamino)pyridine / Ambient temperature

2: 87 percent / p-TsOH, H₂O / acetone / 2 h / 56 °C

4: 66 percent / Et₃N / 20 h / Ambient temperature

5: 1) s-Bu₃BHLi, 2) H₂O₂ / 1) THF, -78 deg C, 30 min, 2) THF, H₂O, to r.t.

6: KOH / methanol / 2 h / 60 °C

7: 99 percent / imidazole / dimethylformamide / 3 h / 80 °C

8: VO(acac)2, tert-butylhydroperoxide / CH₂Cl₂ / 3 h / 0 °C

9: 89 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 48 h / Ambient temperature

10: 67 percent / CrO₃, AcOH / CH₂Cl₂; H₂O / 2 h

11: 1) 2,6-lutidine, trimethylsilyl trifluoromethanesulfonate, 2) Bu₄NF, AcOH / 1) CH₂Cl₂, -60 deg C to 10 deg C, 2 h, 2) THF, 30 min

12: 86 percent / N,N-diethyl-N<<(methoxycarbonyl)amino>sulfonyl>ethanaminium hydroxide / benzene / 0.25 h / 80 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; chromium(VI) oxide; tert.-butylhydroperoxide; dmap; potassium hydroxide; methoxycarbonylsulfamoyl-triethylammmonium hydroxide; bis(acetylacetonate)oxovanadium; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; L-Selectride; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00052a029

Reference yield:

(1S,4S)-1-((R)-2-Benzyloxy-but-3-enyl)-4-methyl-cyclohex-2-enol (143842-76-6) → (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (143842-95-9)

Guidance literature:

Multi-step reaction with 20 steps

1: 92 percent / 48 h / 130 °C

2: 1) disiamylborane, BH₃*SMe₂, 2) 30percent H₂O₂ / 1) THF, r.t., 30 min, 2) MeOH

3: 84 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.05 h / -30 °C

4: Me₂AlCl, MeOH / CH₂Cl₂; hexane / 0.5 h / -40 deg C to r.t.

5: 99.4 percent / tetrahydrofuran / 2 h / Ambient temperature

6: 64 percent / NH₃ liq., Li / tetrahydrofuran / 1 h

7: 1) KOtBu / 1) THF, r.t., 1 h, 2) THF, r.t., 15 min

8: Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

9: pyridine, 4-(N,N-dimethylamino)pyridine / Ambient temperature

10: 87 percent / p-TsOH, H₂O / acetone / 2 h / 56 °C

12: 66 percent / Et₃N / 20 h / Ambient temperature

13: 1) s-Bu₃BHLi, 2) H₂O₂ / 1) THF, -78 deg C, 30 min, 2) THF, H₂O, to r.t.

14: KOH / methanol / 2 h / 60 °C

15: 99 percent / imidazole / dimethylformamide / 3 h / 80 °C

16: VO(acac)2, tert-butylhydroperoxide / CH₂Cl₂ / 3 h / 0 °C

17: 89 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 48 h / Ambient temperature

18: 67 percent / CrO₃, AcOH / CH₂Cl₂; H₂O / 2 h

19: 1) 2,6-lutidine, trimethylsilyl trifluoromethanesulfonate, 2) Bu₄NF, AcOH / 1) CH₂Cl₂, -60 deg C to 10 deg C, 2 h, 2) THF, 30 min

20: 86 percent / N,N-diethyl-N<<(methoxycarbonyl)amino>sulfonyl>ethanaminium hydroxide / benzene / 0.25 h / 80 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; chromium(VI) oxide; methanol; tert.-butylhydroperoxide; dmap; potassium hydroxide; methoxycarbonylsulfamoyl-triethylammmonium hydroxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; water; dihydrogen peroxide; dimethylaluminum chloride; bis-(1,2-dimethylpropyl)borane; lithium; L-Selectride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00052a029

upstream raw materials:

(S)-2-Methyl-butyric acid (1S,3S,5S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-5-hydroxy-7-methyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

(1S,4S)-1-((R)-2-Benzyloxy-but-3-enyl)-4-methyl-cyclohex-2-enol

(3R,5S,8S)-3-Benzyloxy-8-methyl-1-oxa-spiro[4.5]dec-6-en-2-ol

(1S,3R,7S,8S,8aR)-8-[2-((2R,4R,6S)-4-Hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1,3-diol

Downstream raw materials:

pravastatin lactone

Refernces