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

Base Information

Chemical Name:(4S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-4-naphthol
CAS No.:139230-48-1
Molecular Formula:C₁₉H₂₆O₂
Molecular Weight:286.414
Hs Code.:

Synonyms:

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

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

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

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

: 139230-48-1
(4S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-4-naphthol

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.) Li(s-Bu)3BH (L-selectride), 2.) 10percent aq. NaOH, 30percent H₂O₂ / 1.) THF, -78 deg C, 10 min, 2.) THF, 0 deg C, 12 h

With dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; 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; dihydrogen peroxide; L-Selectride; 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:

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

: 139230-48-1
(4S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-4-naphthol

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.) Li(s-Bu)3BH (L-selectride), 2.) 10percent aq. NaOH, 30percent H₂O₂ / 1.) THF, -78 deg C, 10 min, 2.) THF, 0 deg C, 12 h

With dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; 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; dihydrogen peroxide; L-Selectride; 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:

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

: 139230-48-1
(4S,4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-4-naphthol

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.) Li(s-Bu)3BH (L-selectride), 2.) 10percent aq. NaOH, 30percent H₂O₂ / 1.) THF, -78 deg C, 10 min, 2.) THF, 0 deg C, 12 h

With palladium diacetate; sodium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; chloro-trimethyl-silane; cerium(III) chloride; water; dihydrogen peroxide; L-Selectride; 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