(1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde

Base Information

Chemical Name:(1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde
CAS No.:237406-34-7
Molecular Formula:C₂₂H₂₄O₂S
Molecular Weight:352.497
Hs Code.:

Synonyms:(1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde

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Chemical Property of (1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde

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Technology Process of (1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde

There total 17 articles about (1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde 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: 94.0%

: 237406-32-5
((1R,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-methanol

: 237406-34-7
(1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.) 0 deg C, 1 h, 2.) room temp., 4 h;
DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

: 115513-10-5
((S)-2-Methoxy-1,5-dimethyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

: 237406-34-7
(1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde

Guidance literature:: Multi-step reaction with 13 steps

1: 91 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature

2: 100 percent / NaBH₄, ZnCl₂ / tetrahydrofuran / 1 h / -60 - -15 °C

3: 63 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.) room temp., 24 h, 2.) reflux, 3 d

4: 90 percent / I₂ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

5: 98 percent / DIBAL-H / CH₂Cl₂ / 1.) -10 deg C, 15 min, 2.) 0 deg C, 15 min

6: 99 percent / 1,5-diazabicyclo<5.4.0>undecene-5 / CH₂Cl₂ / 1 h / Ambient temperature

7: 94 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

8: Et₂NLi / diethyl ether / Heating

9: 95 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / Ambient temperature

10: 98 percent / SOCl₂, pyridine / diethyl ether / 0.05 h / 0 °C

11: 88 percent / tetrahydrofuran / 1.5 h / Ambient temperature

12: 98 percent / Bu₄NF / tetrahydrofuran / 18 h / Ambient temperature

13: 94 percent / SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temp., 4 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; pyridine-SO₃ complex; lithium diethylamide; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

: 237406-09-6
(2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

: 237406-34-7
(1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde

Guidance literature:: Multi-step reaction with 14 steps

1: n-BuLi, HMPA / tetrahydrofuran; hexane / 1.5 h / -78 °C

2: 91 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature

3: 100 percent / NaBH₄, ZnCl₂ / tetrahydrofuran / 1 h / -60 - -15 °C

4: 63 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.) room temp., 24 h, 2.) reflux, 3 d

5: 90 percent / I₂ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

6: 98 percent / DIBAL-H / CH₂Cl₂ / 1.) -10 deg C, 15 min, 2.) 0 deg C, 15 min

7: 99 percent / 1,5-diazabicyclo<5.4.0>undecene-5 / CH₂Cl₂ / 1 h / Ambient temperature

8: 94 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

9: Et₂NLi / diethyl ether / Heating

10: 95 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / Ambient temperature

11: 98 percent / SOCl₂, pyridine / diethyl ether / 0.05 h / 0 °C

12: 88 percent / tetrahydrofuran / 1.5 h / Ambient temperature

13: 98 percent / Bu₄NF / tetrahydrofuran / 18 h / Ambient temperature

14: 94 percent / SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temp., 4 h

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; n-butyllithium; thionyl chloride; pyridine-SO₃ complex; lithium diethylamide; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water;
DOI:10.1016/S0040-4020(99)00305-1