(1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

Base Information

• Chemical Name: (1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol
• CAS No.: 222545-25-7
• Molecular Formula: C₃₀H₄₀O₆
• Molecular Weight: 496.644

Synonyms:(1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

Chemical Property of (1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

There total 28 articles about (1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-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: 91.0%

(1R,2R,3S,4S)-2-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-1,2-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol (222545-24-6) → (1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol (222545-25-7)

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In decane; dichloromethane; at -8 ℃; for 5h;

DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol (222545-25-7)

Guidance literature:

Multi-step reaction with 28 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

27: 84 percent / n-Bu₄NF / tetrahydrofuran / 168 h / Ambient temperature

28: 91 percent / VO(acac)2, t-BuOOH / CH₂Cl₂; decane / 5 h / -8 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; borane-THF; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tetrabutyl ammonium fluoride; 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; decane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

methyl 2,3-di-O-(4-methoxyphenylmethyl)-α-D-glucopyranoside (222545-13-3) → (1R,2R,3S,4S)-2-<(2R,3S)-3-(3-methyl-2-buten-1-yl)-2-methyloxiran-2-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol (222545-25-7)

Guidance literature:

Multi-step reaction with 26 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: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

19: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

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

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

22: 93 percent / DIBAL / toluene / 0.25 h / -78 °C

23: 93 percent / collidine, LiCl, MsCl / dimethylformamide / 1.5 h / Ambient temperature

24: 60 percent / Pd(PPh₃)4 / tetrahydrofuran / 144 h / 40 °C

25: 84 percent / n-Bu₄NF / tetrahydrofuran / 168 h / Ambient temperature

26: 91 percent / VO(acac)2, t-BuOOH / CH₂Cl₂; decane / 5 h / -8 °C

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

DOI:10.1016/S0040-4020(99)00004-6

upstream raw materials:

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

p-methoxybenzyl chloride

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

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

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