(2RS,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methyl-2-naphthol

Base Information

Chemical Name:(2RS,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methyl-2-naphthol
CAS No.:139230-42-5
Molecular Formula:C₁₉H₂₄O₂
Molecular Weight:284.398
Hs Code.:

Synonyms:

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Chemical Property of (2RS,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methyl-2-naphthol

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Technology Process of (2RS,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methyl-2-naphthol

There total 12 articles about (2RS,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methyl-2-naphthol 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: 100.0%

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

: 139230-42-5,139230-50-5
(2RS,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methyl-2-naphthol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; for 0.5h; Ambient temperature;
DOI:10.1016/S0957-4166(00)80028-2

Reference yield:

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

: 139230-42-5,139230-50-5
(2RS,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methyl-2-naphthol

Guidance literature:: Multi-step reaction with 10 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

With dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; 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; 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; methanol; 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

: 139230-42-5,139230-50-5
(2RS,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,4a,5,6,8a-hexahydro-6-methyl-2-naphthol

Guidance literature:: Multi-step reaction with 11 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

With dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; 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; 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; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; Petroleum ether;
DOI:10.1016/S0957-4166(00)80028-2