(1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime

Base Information

• Chemical Name: (1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime
• CAS No.: 237406-26-7
• Molecular Formula: C₃₃H₄₁NO₆S
• Molecular Weight: 579.758

Synonyms:(1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime

Chemical Property of (1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime

There total 25 articles about (1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime 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:

((S)-2-Methoxy-1,5-dimethyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (115513-10-5) → (1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime (237406-26-7)

Guidance literature:

Multi-step reaction with 20 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

17: NaHCO₃, Dess-Martin reagent / CH₂Cl₂ / 2 h / Ambient temperature

18: 85 percent / Na₂WO₄*2H₂O, aq. H₂O₂ / CH₂Cl₂ / 4 h / Ambient temperature

19: aq. HCl / tetrahydrofuran / 1.5 h / Ambient temperature

20: HONH₂*HCl, Et₃N / ethanol / 1.5 h / Ambient temperature

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

DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

(2'S,2S)-2,4-dimethyl-2-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-3-cyclohexen-1-one (237406-10-9) → (1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime (237406-26-7)

Guidance literature:

Multi-step reaction with 19 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

16: NaHCO₃, Dess-Martin reagent / CH₂Cl₂ / 2 h / Ambient temperature

17: 85 percent / Na₂WO₄*2H₂O, aq. H₂O₂ / CH₂Cl₂ / 4 h / Ambient temperature

18: aq. HCl / tetrahydrofuran / 1.5 h / Ambient temperature

19: HONH₂*HCl, Et₃N / ethanol / 1.5 h / Ambient temperature

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

DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

(2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (237406-09-6) → (1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-5-hydroxy-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde oxime (237406-26-7)

Guidance literature:

Multi-step reaction with 21 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

18: NaHCO₃, Dess-Martin reagent / CH₂Cl₂ / 2 h / Ambient temperature

19: 85 percent / Na₂WO₄*2H₂O, aq. H₂O₂ / CH₂Cl₂ / 4 h / Ambient temperature

20: aq. HCl / tetrahydrofuran / 1.5 h / Ambient temperature

21: HONH₂*HCl, Et₃N / ethanol / 1.5 h / Ambient temperature

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium tungstate; n-butyllithium; thionyl chloride; pyridine-SO₃ complex; hydroxylamine hydrochloride; lithium diethylamide; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; toluene;

DOI:10.1016/S0040-4020(99)00305-1

upstream raw materials:

2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-hydroxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanone

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

(+)-3-bromo-2,2,4-trimethyl-6-oxabicyclo<3.2.1>oct-3-en-7-one

(+)-3-bromo-2,2,4-trimethyl-6-oxa-7-methoxybicyclo<3.2.1>oct-3-ene

Downstream raw materials:

(1R,5S)-3-[2-((1S,6S)-3-Benzenesulfonylmethyl-6-benzyloxy-1-methyl-cyclohex-2-enyl)-acetyl]-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-7-one oxime

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