(1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

Base Information

Chemical Name:(1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane
CAS No.:222545-23-5
Molecular Formula:C₃₆H₅₄O₅Si
Molecular Weight:594.907
Hs Code.:

Synonyms:(1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

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Chemical Property of (1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

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Technology Process of (1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

There total 26 articles about (1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane 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: 60.0%

: 66680-86-2
isobutenyltributyltin

: 222545-22-4
(1S,2S,3S,4R)-3-<(1E)-3-chloro-1-methylprop-1-en-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

: 222545-23-5
(1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

Guidance literature:: tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 40 ℃; for 144h;
DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 222545-23-5
(1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

Guidance literature:: Multi-step reaction with 26 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) room temperature, 20 h

2: 89 percent / AcOH / H₂O / 2 h / 60 °C

3: 93 percent / PPh₃, imidazole, I₂ / toluene / 5 h / Ambient temperature

4: 1.) t-BuOK, 2.) pyridine / 1.) THF, room temperature, 23 h, 2.) room temperature, 3 h

5: 100 percent / Hg(OCOCF₃)2 / acetone; H₂O / 15 h / Ambient temperature

6: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

7: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

8: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

9: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

10: 1.) NaH, imidazole / 1.) THF, 0 deg C, 40 min, 2.) 0 deg C, 1.5 h, 3.) 0 deg C, 30 min

11: 71 percent / AIBN, n-Bu₃SnH / toluene / 15 h / Heating

12: 96 percent / PPTS / ethanol / 3 h / 50 °C

13: 74 percent / propionic acid / 2 h / 140 °C

14: 205 mg / t-BuOK / dimethylsulfoxide / 0.42 h / Ambient temperature

15: 87 percent / aq. NaHCO₃, KI, I₂ / tetrahydrofuran / 2 h / Ambient temperature

16: 91 percent / AIBN, n-Bu₃SnH / benzene / 2 h / Ambient temperature

17: DIBAL / toluene / 0.17 h / -78 °C

18: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, 60 deg C, 3 h

19: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

20: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) 0 deg C, 1 h

21: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

22: KN(SiMe₃)2, Et₃N / tetrahydrofuran / 0.33 h / 0 °C

23: Pd)OAc)2 / acetonitrile / 12 h / 0 °C

24: 93 percent / DIBAL / toluene / 0.25 h / -78 °C

25: 93 percent / collidine, LiCl, MsCl / dimethylformamide / 1.5 h / Ambient temperature

26: 60 percent / Pd(PPh₃)4 / tetrahydrofuran / 144 h / 40 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,3,5-trimethyl-pyridine; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; borane-THF; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; sodium methylate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; propionic acid; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; potassium iodide; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

: 210765-01-8
(1R,2R,3S,4S)-2-<(1R)-1-methylprop-2-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

: 222545-23-5
(1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) 0 deg C, 1 h

3: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

4: KN(SiMe₃)2, Et₃N / tetrahydrofuran / 0.33 h / 0 °C

5: Pd)OAc)2 / acetonitrile / 12 h / 0 °C

6: 93 percent / DIBAL / toluene / 0.25 h / -78 °C

7: 93 percent / collidine, LiCl, MsCl / dimethylformamide / 1.5 h / Ambient temperature

8: 60 percent / Pd(PPh₃)4 / tetrahydrofuran / 144 h / 40 °C

With 2,6-dimethylpyridine; 2,3,5-trimethyl-pyridine; palladium diacetate; sodium hydroxide; tetrapropylammonium perruthennate; borane-THF; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(99)00004-6