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

Base Information

Chemical Name:(1R,2R,3S,4S)-2-<(1E)-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol
CAS No.:222545-30-4
Molecular Formula:C₂₆H₃₄O₅
Molecular Weight:426.553
Hs Code.:

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

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Chemical Property of (1R,2R,3S,4S)-2-<(1E)-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

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Technology Process of (1R,2R,3S,4S)-2-<(1E)-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

There total 18 articles about (1R,2R,3S,4S)-2-<(1E)-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol 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: 86.0%

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

: 222545-30-4
(1R,2R,3S,4S)-2-<(1E)-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

Guidance literature:: With Wilkinson's catalyst; In ethanol; benzene; at 120 ℃; for 48h;
DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

: 222545-13-3
methyl 2,3-di-O-(4-methoxyphenylmethyl)-α-D-glucopyranoside

: 222545-30-4
(1R,2R,3S,4S)-2-<(1E)-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

Guidance literature:: Multi-step reaction with 17 steps

1: 93 percent / PPh₃, imidazole, I₂ / toluene / 5 h / Ambient temperature

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

3: 100 percent / Hg(OCOCF₃)2 / acetone; H₂O / 15 h / Ambient temperature

4: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

5: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

6: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

7: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

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

9: 71 percent / AIBN, n-Bu₃SnH / toluene / 15 h / Heating

10: 96 percent / PPTS / ethanol / 3 h / 50 °C

11: 74 percent / propionic acid / 2 h / 140 °C

12: 205 mg / t-BuOK / dimethylsulfoxide / 0.42 h / Ambient temperature

13: 87 percent / aq. NaHCO₃, KI, I₂ / tetrahydrofuran / 2 h / Ambient temperature

14: 91 percent / AIBN, n-Bu₃SnH / benzene / 2 h / Ambient temperature

15: DIBAL / toluene / 0.17 h / -78 °C

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

17: 86 percent / (PPh₃)3RhCl / ethanol; benzene / 48 h / 120 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; iodine; tri-n-butyl-tin hydride; sodium methylate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; propionic acid; methanesulfonyl chloride; triphenylphosphine; potassium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; toluene; benzene;
DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

: 199918-03-1
methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside

: 222545-30-4
(1R,2R,3S,4S)-2-<(1E)-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

Guidance literature:: Multi-step reaction with 18 steps

1: 89 percent / AcOH / H₂O / 2 h / 60 °C

2: 93 percent / PPh₃, imidazole, I₂ / toluene / 5 h / Ambient temperature

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

4: 100 percent / Hg(OCOCF₃)2 / acetone; H₂O / 15 h / Ambient temperature

5: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

6: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

7: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

8: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

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

10: 71 percent / AIBN, n-Bu₃SnH / toluene / 15 h / Heating

11: 96 percent / PPTS / ethanol / 3 h / 50 °C

12: 74 percent / propionic acid / 2 h / 140 °C

13: 205 mg / t-BuOK / dimethylsulfoxide / 0.42 h / Ambient temperature

14: 87 percent / aq. NaHCO₃, KI, I₂ / tetrahydrofuran / 2 h / Ambient temperature

15: 91 percent / AIBN, n-Bu₃SnH / benzene / 2 h / Ambient temperature

16: DIBAL / toluene / 0.17 h / -78 °C

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

18: 86 percent / (PPh₃)3RhCl / ethanol; benzene / 48 h / 120 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; iodine; tri-n-butyl-tin hydride; sodium methylate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; propionic acid; methanesulfonyl chloride; triphenylphosphine; potassium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; toluene; benzene;
DOI:10.1016/S0040-4020(99)00004-6