(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-one

Base Information

Chemical Name:(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-one
CAS No.:139230-34-5
Molecular Formula:C₁₉H₂₂O₂
Molecular Weight:282.382
Hs Code.:

Synonyms:(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-one

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Chemical Property of (4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-one

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Technology Process of (4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-one

There total 10 articles about (4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-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:

: 139230-36-7
4,4-(trimethylenedithio)-(E,E)-6,8-decadienal

: 139230-34-5
(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-one

Guidance literature:: Multi-step reaction with 9 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

With dmap; palladium diacetate; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; 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; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; p-benzoquinone; sodium iodide; copper(II) oxide; copper dichloride; In tetrahydrofuran; dichloromethane; acetone; toluene; Petroleum ether;
DOI:10.1016/S0957-4166(00)80028-2

Reference yield:

: 139230-32-3
4,4-(trimethylenedithio)-(E,E)-6,8-decadien-1-ol

: 139230-34-5
(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-one

Guidance literature:: Multi-step reaction with 10 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

With dmap; palladium diacetate; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; 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; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; p-benzoquinone; sodium iodide; copper(II) oxide; copper dichloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetone; toluene; Petroleum ether;
DOI:10.1016/S0957-4166(00)80028-2

Reference yield:

: 139230-39-0
(1S,2S,4aR,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6,6-(trimethylenedithio)-1-naphthalenemethanol

: 139230-34-5
(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methylnaphthalen-2-one

Guidance literature:: Multi-step reaction with 3 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

With palladium diacetate; chloro-trimethyl-silane; water; sodium hydride; triethylamine; p-benzoquinone; sodium iodide; copper(II) oxide; copper dichloride; In acetone;
DOI:10.1016/S0957-4166(00)80028-2