(E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol

Base Information

• Chemical Name: (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol
• CAS No.: 114972-63-3
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• Mol file: 114972-63-3.mol

Synonyms:(E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol

Chemical Property of (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol

There total 11 articles about (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-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: 98.0%

((E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-enyloxy)-tert-butyl-dimethyl-silane (114972-62-2) → (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol (114972-63-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 1) 0 deg C, 1 h, 2) room temperature, 2 h;

DOI:10.1016/S0040-4020(01)90315-1

Reference yield:

(2S,3S)-1-(benzyloxy)-4-[(tert-butyldimethylsilyl)oxy]-3-methylbutan-2-ol (114972-44-0) → (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol (114972-63-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / H₂ / Pd(OH)2/C / ethanol / 4 h

2: 92 percent / pyridine / -20 °C

3: 84 percent / LiB(Et)3H / tetrahydrofuran / 0.5 h / 0 °C

4: 72 percent / diisopropylethyl amine / CH₂Cl₂ / Ambient temperature

5: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

6: 92 percent / CBr₄/PPh₃ / CH₂Cl₂ / 1 h / -40 °C

7: 80 percent / tetrabutylammonium bromide / dimethylformamide / 8 h / 40 °C

8: 1) butyllithium, HMPA, / 1) THF, hexane, -40 deg C, 90 min, -65 deg C, 10 min, 2) THF, -65 deg C - -10 deg C, 2.5 h

9: 87 percent / Na₂HPO₄, 6percent Na-amalgam / methanol / 2 h / Ambient temperature

10: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; carbon tetrabromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90315-1

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-en-1-ol (114972-63-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / diisopropylethyl amine / CH₂Cl₂ / Ambient temperature

2: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

3: 92 percent / CBr₄/PPh₃ / CH₂Cl₂ / 1 h / -40 °C

4: 80 percent / tetrabutylammonium bromide / dimethylformamide / 8 h / 40 °C

5: 1) butyllithium, HMPA, / 1) THF, hexane, -40 deg C, 90 min, -65 deg C, 10 min, 2) THF, -65 deg C - -10 deg C, 2.5 h

6: 87 percent / Na₂HPO₄, 6percent Na-amalgam / methanol / 2 h / Ambient temperature

7: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; carbon tetrabromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90315-1

upstream raw materials:

((E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-enyloxy)-tert-butyl-dimethyl-silane

Benzyloxymethyl chloride

(2R,3S)-4-((tert-butyldimethylsilyl)oxy)-3-methylbutan-2-ol

(2S,3S)-4-[(tert-butyldimethylsilyl)oxy]-3-methylbutane-1,2-diol

Downstream raw materials:

(E)-(2R,7S,8R)-8-Benzyloxymethoxy-2-methoxy-3,7-dimethyl-non-3-enal

(-)-albocycline

(2E,5E,8E)-(4R,7S,12S,13R)-13-Benzyloxymethoxy-7-methoxy-4,8,12-trimethyl-4-(tetrahydro-pyran-2-yloxy)-tetradeca-2,5,8-trienoic acid

(2E,5E,8E)-(4R,7S,12S,13R)-13-Benzyloxymethoxy-7-methoxy-4,8,12-trimethyl-4-(tetrahydro-pyran-2-yloxy)-tetradeca-2,5,8-trienoic acid methyl ester