(1'S,2'S,4a'R,8'S,8a'S)-3-<2'-methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl>propyl (R)-O-methylmandelate

Base Information

• Chemical Name: (1'S,2'S,4a'R,8'S,8a'S)-3-<2'-methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl>propyl (R)-O-methylmandelate
• CAS No.: 143112-41-8
• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.623

Synonyms:

Chemical Property of (1'S,2'S,4a'R,8'S,8a'S)-3-<2'-methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl>propyl (R)-O-methylmandelate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (1'S,2'S,4a'R,8'S,8a'S)-3-<2'-methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl>propyl (R)-O-methylmandelate

There total 26 articles about (1'S,2'S,4a'R,8'S,8a'S)-3-<2'-methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl>propyl (R)-O-methylmandelate 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:

(S)-(+)-2-methylbutyric anhydride (84131-91-9) + (1'S,2'S,4a'R,8'S,8a'S)-3-(8'-hydroxy-2'-methyl-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl)propyl (R)-O-methylmandelate (143112-40-7) → (1'S,2'S,4a'R,8'S,8a'S)-3-<2'-methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl>propyl (R)-O-methylmandelate (143112-41-8)

Guidance literature:

With pyridine; at 40 ℃;

DOI:10.1039/c39920000866

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) → (1'S,2'S,4a'R,8'S,8a'S)-3-<2'-methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl>propyl (R)-O-methylmandelate (143112-41-8)

Guidance literature:

Multi-step reaction with 16 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

With pyridine; methanol; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; hydrogen fluoride; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; magnesium; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;

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) → (1'S,2'S,4a'R,8'S,8a'S)-3-<2'-methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl>propyl (R)-O-methylmandelate (143112-41-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1039/P19940002417

upstream raw materials:

(S)-(+)-2-methylbutyric anhydride

(1'S,2'S,4a'R,8'S,8a'S)-3-(8'-hydroxy-2'-methyl-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl)propyl (R)-O-methylmandelate

(R)-methoxyphenylacetic acid

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

Downstream raw materials:

(+)-dihydrocompactin

(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

(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

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