(1R,2R,3S,4S)-2-<(1E)-3-hydroxy-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)-3-hydroxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol
• CAS No.: 210765-05-2
• Molecular Formula: C₂₆H₃₄O₆
• Molecular Weight: 442.552
• Mol file: 210765-05-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 23 articles about (1R,2R,3S,4S)-2-<(1E)-3-hydroxy-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:

(3S,3aR,4S,5S,7aR)-4,5-Bis-(4-methoxy-benzyloxy)-3-methyl-octahydro-benzofuran-2-ol (222545-34-8) → (1R,2R,3S,4S)-2-<(1E)-3-hydroxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol (210765-05-2)

Guidance literature:

Multi-step reaction with 8 steps

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

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

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

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

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

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

7: 93 percent / DIBAL / toluene / 0.25 h / -78 °C

8: 100 percent / n-Bu₃NF / tetrahydrofuran / 144 h / Ambient temperature

With 2,6-dimethylpyridine; palladium diacetate; sodium hydroxide; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; n-Bu₃NF; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

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

Reference yield:

(4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one (210764-93-5) → (1R,2R,3S,4S)-2-<(1E)-3-hydroxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol (210765-05-2)

Guidance literature:

Multi-step reaction with 19 steps

1: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

2: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

3: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

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

5: 71 percent / AIBN, n-Bu₃SnH / toluene / 15 h / Heating

6: 96 percent / PPTS / ethanol / 3 h / 50 °C

7: 74 percent / propionic acid / 2 h / 140 °C

8: 205 mg / t-BuOK / dimethylsulfoxide / 0.42 h / Ambient temperature

9: 87 percent / aq. NaHCO₃, KI, I₂ / tetrahydrofuran / 2 h / Ambient temperature

10: 91 percent / AIBN, n-Bu₃SnH / benzene / 2 h / Ambient temperature

11: DIBAL / toluene / 0.17 h / -78 °C

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

13: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

15: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

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

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

18: 93 percent / DIBAL / toluene / 0.25 h / -78 °C

19: 100 percent / n-Bu₃NF / tetrahydrofuran / 144 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; borane-THF; 2,2'-azobis(isobutyronitrile); n-Bu₃NF; potassium tert-butylate; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; sodium methylate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; propionic acid; 4-methylmorpholine N-oxide; triethylamine; potassium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; benzene;

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

Reference yield:

ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate (210764-98-0) → (1R,2R,3S,4S)-2-<(1E)-3-hydroxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol (210765-05-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 205 mg / t-BuOK / dimethylsulfoxide / 0.42 h / Ambient temperature

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

3: 91 percent / AIBN, n-Bu₃SnH / benzene / 2 h / Ambient temperature

4: DIBAL / toluene / 0.17 h / -78 °C

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

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

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

8: 81 percent / MS-4A, tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / Ambient temperature

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

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

11: 93 percent / DIBAL / toluene / 0.25 h / -78 °C

12: 100 percent / n-Bu₃NF / tetrahydrofuran / 144 h / Ambient temperature

With 2,6-dimethylpyridine; palladium diacetate; sodium hydroxide; n-butyllithium; tetrapropylammonium perruthennate; borane-THF; 2,2'-azobis(isobutyronitrile); n-Bu₃NF; potassium tert-butylate; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; potassium iodide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; benzene;

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

upstream raw materials:

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

(1R,4S,5S)-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-ol

Downstream raw materials:

(2S,3S,4S)-2-<(1E)-3-(tert-butyldimethylsilyl)oxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-one

(2E)-3-<(3R,4S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-1-oxaspiro<2.5>oct-4-yl>-1-(tert-butyldimethylsilyl)oxybut-2-ene

FR65814

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