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

Base Information

Chemical Name:(1'R,2'R,4a'S,8'R,8a'R)-3-(8'-hydroxy-2'-methyl-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl)propyl (R)-O-methylmandelate
CAS No.:143112-48-5
Molecular Formula:C₂₃H₃₂O₄
Molecular Weight:372.505
Hs Code.:

Synonyms:

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

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

There total 23 articles about (1'R,2'R,4a'S,8'R,8a'R)-3-(8'-hydroxy-2'-methyl-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:

: 136967-16-3,143112-25-8,143112-26-9
methyl (1R*,2S*,4aS*,8R*,8aS*)-8-(tert-butyldimethylsiloxy)-2-methyl-4-oxodecahydronaphthalene-1-carboxylate

: 143112-48-5
(1'R,2'R,4a'S,8'R,8a'R)-3-(8'-hydroxy-2'-methyl-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl)propyl (R)-O-methylmandelate

Guidance literature:: Multi-step reaction with 15 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: 48 percent / 1,3-dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH₂Cl₂

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:

: 143112-32-7
(2aR*,3S*,5aR*,8aS*,8bS*)-3-methyl-3,3a,5a,6,7,8,8a,8b-octahydro-1-oxaacenaphthen-2-one

: 143112-48-5
(1'R,2'R,4a'S,8'R,8a'R)-3-(8'-hydroxy-2'-methyl-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl)propyl (R)-O-methylmandelate

Guidance literature:: Multi-step reaction with 10 steps

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

2: 1.24 g / pyridine / 1 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

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

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

6: 55.4 percent / potassium carbonate / methanol / Ambient temperature

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

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

9: 92 percent / aq. HF / acetonitrile / 1 h / Ambient temperature

10: 48 percent / 1,3-dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH₂Cl₂

With pyridine; methanol; dmap; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen fluoride; sodium hydride; potassium carbonate; magnesium; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1039/P19940002417

Reference yield:

: 143125-96-6
<(1R*,2S*,4aR*,8S*,8aS*)-8-(tert-butyldimethylsiloxy)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl>methyl pivalate

: 143112-48-5
(1'R,2'R,4a'S,8'R,8a'R)-3-(8'-hydroxy-2'-methyl-1',2',4a',5',6',7',8',8a'-octahydronaphthalen-1'-yl)propyl (R)-O-methylmandelate

Guidance literature:: Multi-step reaction with 7 steps

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

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

3: 55.4 percent / potassium carbonate / methanol / Ambient temperature

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

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

6: 92 percent / aq. HF / acetonitrile / 1 h / Ambient temperature

7: 48 percent / 1,3-dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH₂Cl₂

With methanol; dmap; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen fluoride; sodium hydride; potassium carbonate; magnesium; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1039/P19940002417