(2S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-2,6-dimethylnaphthalen-4-one

Base Information

• Chemical Name: (2S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-2,6-dimethylnaphthalen-4-one
• CAS No.: 139230-46-9
• Molecular Formula: C₂₀H₂₆O₂
• Molecular Weight: 298.425

Synonyms:

Chemical Property of (2S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-2,6-dimethylnaphthalen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-2,6-dimethylnaphthalen-4-one

There total 15 articles about (2S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-2,6-dimethylnaphthalen-4-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:

4,4-(trimethylenedithio)-(E,E)-6,8-decadienal (139230-36-7) → (2S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-2,6-dimethylnaphthalen-4-one (139230-46-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) hexamethyldisilazane, n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 30 min

2: Et₃N, dimethylaminopyridine / CH₂Cl₂ / 0 °C

3: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂ / 0.5 h / 0 °C

4: 70 percent / 1,1,4,4-tetraphenyl-2,3-O-(1-phenyl-ethane-1,1-diyl)-D-threitol, dichlorodiisopropoxytitanium, molecular sieves 4A / toluene; petroleum ether / 150 h / Ambient temperature

5: 1.) n-butyllithium / 1.) THF, hexane, from -23 deg C to 0 deg C, 2.) THF, hexane, 0 deg C, 1 h

6: 98 percent / LiAlH₄ / tetrahydrofuran / 12 h / Ambient temperature

7: 1.) NaH, 2.) NaI / 1.) THF, 0 deg C, 2.) THF, RT, 12 h

8: 80 percent / CuCl₂, CuO, H₂O / acetone / 1 h / Heating

9: 1.) trimethylsilyl chloride, Et₃N, NaI, 2.) Pd(OAc)2, p-benzoquinone / 1.) CH₃CN, 40 deg C, 5 h, 2.) CH₃CN,RT, 24 h

10: 100 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / Ambient temperature

11: 81 percent / nBu₄NReO₄, p-toluenesulfonic acid / CH₂Cl₂ / 0.08 h / Ambient temperature

12: 97 percent / pyridinium dichromate (PDC) / CH₂Cl₂ / 48 h / Ambient temperature

13: 1.) CuI / 1.) Et₂O, -23 deg C, 20 min, 2.) Et₂O, -78 deg C, 5 min

With dmap; palladium diacetate; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; chloro-trimethyl-silane; cerium(III) chloride; titanium(IV) dichlorodiisopropylate; 1,1,4,4-tetraphenyl-2,3-O-(1-phenyl-ethane-1,1-diyl)-D-threitol; 4 A molecular sieve; water; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tetrabutylammonium perrhenate; 1,1,1,3,3,3-hexamethyl-disilazane; p-benzoquinone; sodium iodide; copper(II) oxide; copper dichloride; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; Petroleum ether;

DOI:10.1016/S0957-4166(00)80028-2

Reference yield:

4,4-(trimethylenedithio)-(E,E)-6,8-decadien-1-ol (139230-32-3) → (2S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-2,6-dimethylnaphthalen-4-one (139230-46-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 85 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide / 1 h / Ambient temperature

2: 1.) hexamethyldisilazane, n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 30 min

3: Et₃N, dimethylaminopyridine / CH₂Cl₂ / 0 °C

4: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂ / 0.5 h / 0 °C

5: 70 percent / 1,1,4,4-tetraphenyl-2,3-O-(1-phenyl-ethane-1,1-diyl)-D-threitol, dichlorodiisopropoxytitanium, molecular sieves 4A / toluene; petroleum ether / 150 h / Ambient temperature

6: 1.) n-butyllithium / 1.) THF, hexane, from -23 deg C to 0 deg C, 2.) THF, hexane, 0 deg C, 1 h

7: 98 percent / LiAlH₄ / tetrahydrofuran / 12 h / Ambient temperature

8: 1.) NaH, 2.) NaI / 1.) THF, 0 deg C, 2.) THF, RT, 12 h

9: 80 percent / CuCl₂, CuO, H₂O / acetone / 1 h / Heating

10: 1.) trimethylsilyl chloride, Et₃N, NaI, 2.) Pd(OAc)2, p-benzoquinone / 1.) CH₃CN, 40 deg C, 5 h, 2.) CH₃CN,RT, 24 h

11: 100 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / Ambient temperature

12: 81 percent / nBu₄NReO₄, p-toluenesulfonic acid / CH₂Cl₂ / 0.08 h / Ambient temperature

13: 97 percent / pyridinium dichromate (PDC) / CH₂Cl₂ / 48 h / Ambient temperature

14: 1.) CuI / 1.) Et₂O, -23 deg C, 20 min, 2.) Et₂O, -78 deg C, 5 min

With dmap; palladium diacetate; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; chloro-trimethyl-silane; cerium(III) chloride; titanium(IV) dichlorodiisopropylate; pyridine-SO₃ complex; 1,1,4,4-tetraphenyl-2,3-O-(1-phenyl-ethane-1,1-diyl)-D-threitol; 4 A molecular sieve; water; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tetrabutylammonium perrhenate; 1,1,1,3,3,3-hexamethyl-disilazane; p-benzoquinone; sodium iodide; copper(II) oxide; copper dichloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; Petroleum ether;

DOI:10.1016/S0957-4166(00)80028-2

Reference yield:

(1S,2S,4aR,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6,6-(trimethylenedithio)-1-naphthalenemethanol (139230-39-0) → (2S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-2,6-dimethylnaphthalen-4-one (139230-46-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH, 2.) NaI / 1.) THF, 0 deg C, 2.) THF, RT, 12 h

2: 80 percent / CuCl₂, CuO, H₂O / acetone / 1 h / Heating

3: 1.) trimethylsilyl chloride, Et₃N, NaI, 2.) Pd(OAc)2, p-benzoquinone / 1.) CH₃CN, 40 deg C, 5 h, 2.) CH₃CN,RT, 24 h

4: 100 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / Ambient temperature

5: 81 percent / nBu₄NReO₄, p-toluenesulfonic acid / CH₂Cl₂ / 0.08 h / Ambient temperature

6: 97 percent / pyridinium dichromate (PDC) / CH₂Cl₂ / 48 h / Ambient temperature

7: 1.) CuI / 1.) Et₂O, -23 deg C, 20 min, 2.) Et₂O, -78 deg C, 5 min

With palladium diacetate; sodium tetrahydroborate; copper(l) iodide; dipyridinium dichromate; chloro-trimethyl-silane; cerium(III) chloride; water; sodium hydride; toluene-4-sulfonic acid; triethylamine; tetrabutylammonium perrhenate; p-benzoquinone; sodium iodide; copper(II) oxide; copper dichloride; In methanol; dichloromethane; acetone;

DOI:10.1016/S0957-4166(00)80028-2

upstream raw materials:

methyllithium

(1S,2S,4aR,8aS)-1-benzyloxymethyl-1,2,4a,5,8,8a-hexahydro-2-methylnaphthalen-8-one

4,4-(trimethylenedithio)-(E,E)-6,8-decadienal

4,4-(trimethylenedithio)-(E,E)-6,8-decadien-1-ol

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