2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol

Base Information

Chemical Name:2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol
CAS No.:237406-19-8
Molecular Formula:C₃₄H₄₄O₄S
Molecular Weight:548.787
Hs Code.:

2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol

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Chemical Property of 2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol

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Technology Process of 2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol

There total 21 articles about 2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol 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:

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

: 237406-19-8
2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol

Guidance literature:: Multi-step reaction with 16 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

14: KHMDS / toluene / 1.) 0 deg C, 1 h, 2.) room temp., 2 h

15: aq. HCl / tetrahydrofuran / 18 h

16: 1.) t-BuLi / 1.) Et₂O, pentane, -78 deg C, 30 min, 2.) Et₂O, pentane, -78 to -20 deg C, 1 h

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

Reference yield:

: 237406-10-9
(2'S,2S)-2,4-dimethyl-2-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-3-cyclohexen-1-one

: 237406-19-8
2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol

Guidance literature:: Multi-step reaction with 15 steps

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

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

3: 90 percent / I₂ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

4: 98 percent / DIBAL-H / CH₂Cl₂ / 1.) -10 deg C, 15 min, 2.) 0 deg C, 15 min

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

6: 94 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

7: Et₂NLi / diethyl ether / Heating

8: 95 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / Ambient temperature

9: 98 percent / SOCl₂, pyridine / diethyl ether / 0.05 h / 0 °C

10: 88 percent / tetrahydrofuran / 1.5 h / Ambient temperature

11: 98 percent / Bu₄NF / tetrahydrofuran / 18 h / Ambient temperature

12: 94 percent / SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temp., 4 h

13: KHMDS / toluene / 1.) 0 deg C, 1 h, 2.) room temp., 2 h

14: aq. HCl / tetrahydrofuran / 18 h

15: 1.) t-BuLi / 1.) Et₂O, pentane, -78 deg C, 30 min, 2.) Et₂O, pentane, -78 to -20 deg C, 1 h

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

: 237406-19-8
2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol

Guidance literature:: Multi-step reaction with 17 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

15: KHMDS / toluene / 1.) 0 deg C, 1 h, 2.) room temp., 2 h

16: aq. HCl / tetrahydrofuran / 18 h

17: 1.) t-BuLi / 1.) Et₂O, pentane, -78 deg C, 30 min, 2.) Et₂O, pentane, -78 to -20 deg C, 1 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; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium hexamethylsilazane; 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; toluene;
DOI:10.1016/S0040-4020(99)00305-1