(1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

Base Information

• Chemical Name: (1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol
• CAS No.: 161358-36-7
• Molecular Formula: C₃₉H₅₈O₅Si
• Molecular Weight: 634.972
• Mol file: 161358-36-7.mol

Synonyms:

Chemical Property of (1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

There total 32 articles about (1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol 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:

methyl (1R*,2S*,4aS*,8R*,8aS*)-8-(tert-butyldimethylsiloxy)-2-methyl-4-oxodecahydronaphthalene-1-carboxylate (136967-16-3,143112-25-8,143112-26-9) → (1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol (161358-36-7)

Guidance literature:

Multi-step reaction with 24 steps

1: 80 percent / NaBH₄ / methanol / 1 h / Ambient temperature

2: 1.) BuLi / 1) THF, hexane, -50 deg C, 15 min; 2) THF, hexane, -30 deg C, 3.) THF, hexane, -25 deg C

3: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

4: 1.) oxalyl dichloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min; 2) CH₂Cl₂, -78 --> -25 deg C

5: 1.) NaBH₄ / 1) CH₃OH, -60 deg C, 3 h, 0 deg C, 30 min; 2) 1-methylnaphthalene, 210 deg C, 1.5 h

6: LiAlH₄ / various solvent(s); diethyl ether / 1 h / Ambient temperature

7: 1.24 g / pyridine / 1 h / Ambient temperature

8: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

9: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

10: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min; 2) Ch₂Cl₂, -78 --> -25 deg C

11: 55.4 percent / potassium carbonate / methanol / Ambient temperature

12: 1.) NaH / 1) THF, 0 deg C, 20 min; 2) THF, HMPA, reflux, 3 h

13: 1.) Mg, CH₃OH, 2.) LiAlH₄ / 1) 0 deg C, overnight; 2) ether, room temperature, 1 h

14: 92 percent / aq. HF / acetonitrile / 1 h / Ambient temperature

15: 37 percent / 1,3-dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH₂Cl₂

16: 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 40 °C

17: 93 percent / KOH / methanol / Ambient temperature

18: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min; 2) CH₂Cl₂, -78 --> -25 deg C

19: 1.) TiCl₄ / 1) CH₂Cl₂, -90 deg C, 15 min; 2) CH₂Cl₂, -90 --> -50 deg C

20: 1.) Et₂BOMe, 2.) NaBH₄ / 1) THF, methanol, room temperature, 15 min; 2) THF, methanol, -78 --> room temperature

21: 26 percent / HF, pyridine / acetonitrile / 1 h / Ambient temperature

22: 79 percent / pyridinium toluene-p-sulfonate / CH₂Cl₂ / Ambient temperature

23: 21.1 mg / LiAlH₄ / diethyl ether / 6.5 h / Ambient temperature

24: Et₃N, 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

With pyridine; methanol; dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl methoxy borane; hydrogen fluoride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; potassium carbonate; magnesium; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/P19940002417

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol (161358-36-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / pyridinium toluene-p-sulfonate / CH₂Cl₂ / Ambient temperature

2: 21.1 mg / LiAlH₄ / diethyl ether / 6.5 h / Ambient temperature

3: Et₃N, 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

With dmap; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; triethylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/P19940002417

Reference yield:

(1'S*,2'S*,4a'R*,8'S*,8a'S*)-8'-hydroxy-2'-methyl-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-propanol (143112-39-4) → (1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol (161358-36-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 37 percent / 1,3-dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH₂Cl₂

2: 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 40 °C

3: 93 percent / KOH / methanol / Ambient temperature

4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min; 2) CH₂Cl₂, -78 --> -25 deg C

5: 1.) TiCl₄ / 1) CH₂Cl₂, -90 deg C, 15 min; 2) CH₂Cl₂, -90 --> -50 deg C

6: 1.) Et₂BOMe, 2.) NaBH₄ / 1) THF, methanol, room temperature, 15 min; 2) THF, methanol, -78 --> room temperature

7: 26 percent / HF, pyridine / acetonitrile / 1 h / Ambient temperature

8: 79 percent / pyridinium toluene-p-sulfonate / CH₂Cl₂ / Ambient temperature

9: 21.1 mg / LiAlH₄ / diethyl ether / 6.5 h / Ambient temperature

10: Et₃N, 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

With pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; diethyl methoxy borane; hydrogen fluoride; pyridinium p-toluenesulfonate; titanium tetrachloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/P19940002417

upstream raw materials:

tert-butylchlorodiphenylsilane

(3R,5S)-7-<(1'S,2'S4a'R,8'S,8a'S)-8'-hydroxy-2'-methyl-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1-yl>-3-(tetrahydropyran-2-yloxy)heptane-1,5-diol

3,4-dihydro-2H-pyran

methyl (1R*,2S*,4aS*,8R*,8aS*)-8-(tert-butyldimethylsiloxy)-2-methyl-4-oxodecahydronaphthalene-1-carboxylate

Downstream raw materials:

(1S,2S,4aR,8S,8aS)-8-acetoxy-1-<(3'S,5'R)-3'-acetoxy-7'-(tert-butyldiphenylsiloxy)-5'-(tetrahydropyran-2-yloxy)heptyl>-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene