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

Base Information

Chemical Name:(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-2,2-(trimethylenedithio)naphthalene
CAS No.:139230-40-3
Molecular Formula:C₂₂H₃₀OS₂
Molecular Weight:374.612
Hs Code.:

Synonyms:(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-2,2-(trimethylenedithio)naphthalene

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

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

There total 10 articles about (4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-2,2-(trimethylenedithio)naphthalene 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:

: 139230-31-2
2-(3-(1,3-dithian-2-yl)propoxy)tetrahydro-2H-pyran

: 139230-40-3
(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-2,2-(trimethylenedithio)naphthalene

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) n-BuLi / 1.) THF, hexane, -23 deg C, 2 h, 2.) THF, hexane, -78 deg C, 12 h

2: 93 percent / 2N aq. HCl, methanol / 12 h / Ambient temperature

3: 85 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide / 1 h / Ambient temperature

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

5: Et₃N, dimethylaminopyridine / CH₂Cl₂ / 0 °C

6: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂ / 0.5 h / 0 °C

7: 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

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

9: 98 percent / LiAlH₄ / tetrahydrofuran / 12 h / Ambient temperature

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

With hydrogenchloride; methanol; dmap; lithium aluminium tetrahydride; n-butyllithium; 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; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 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

: 139230-40-3
(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-2,2-(trimethylenedithio)naphthalene

Guidance literature:: Multi-step reaction with 8 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

With dmap; lithium aluminium tetrahydride; n-butyllithium; 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; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; Petroleum ether;
DOI:10.1016/S0957-4166(00)80028-2

Reference yield:

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

: 139230-40-3
(4aS,5S,6S,8aR)-5-benzyloxymethyl-1,2,3,4,4a,5,6,8a-octahydro-6-methyl-2,2-(trimethylenedithio)naphthalene

Guidance literature:: Multi-step reaction with 7 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

With dmap; lithium aluminium tetrahydride; n-butyllithium; titanium(IV) dichlorodiisopropylate; 1,1,4,4-tetraphenyl-2,3-O-(1-phenyl-ethane-1,1-diyl)-D-threitol; 4 A molecular sieve; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; In tetrahydrofuran; dichloromethane; toluene; Petroleum ether;
DOI:10.1016/S0957-4166(00)80028-2