2α-(2,6-dimethoxyphenoxy)-6α-<4-(trans-3,7-dimethyl-2,6-octadienoxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane

Base Information

• Chemical Name: 2α-(2,6-dimethoxyphenoxy)-6α-<4-(trans-3,7-dimethyl-2,6-octadienoxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane
• CAS No.: 142206-72-2
• Molecular Formula: C₃₄H₄₆O₁₀
• Molecular Weight: 614.733

Synonyms:

Chemical Property of 2α-(2,6-dimethoxyphenoxy)-6α-<4-(trans-3,7-dimethyl-2,6-octadienoxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 2α-(2,6-dimethoxyphenoxy)-6α-<4-(trans-3,7-dimethyl-2,6-octadienoxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane

There total 27 articles about 2α-(2,6-dimethoxyphenoxy)-6α-<4-(trans-3,7-dimethyl-2,6-octadienoxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane 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:

3-benzyloxy-4-(2-methoxyethoxy)phenol (142206-55-1) → 2α-(2,6-dimethoxyphenoxy)-6α-<4-(trans-3,7-dimethyl-2,6-octadienoxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane (142206-72-2)

Guidance literature:

Multi-step reaction with 19 steps

1: 99 percent / NaH / tetrahydrofuran; paraffin / 48 h / Ambient temperature

2: 83 percent / POCl₃ / 1 h / 60 °C

3: 47 percent / i-Pr₂NLi / tetrahydrofuran / 2 h / -75 °C

4: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

5: 67 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

6: 1) 2percent aq. OsO₄, N-methylmorpholine N-oxide, 2) NaIO₄ / 1) acetone, t-BuOH, r.t., 16 h, 2) EtOAc, H₂O, r.t., 2 h

7: 93 percent / Ag₂CO₃, celite / benzene / 0.5 h / Heating

8: 1) Et₃N, MeSO₂Cl, 2) Et₃N / 1) benzene, r.t., 2 h, 2) benzene, r.t., 16 h

9: 98 percent / N-methylmorpholine N-oxide, 2percent aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / Ambient temperature

10: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

11: 57 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

12: 82 percent / H₂ / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

13: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

14: 69 percent / DIBAL-H / toluene / 0.5 h / -75 °C

15: 74 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

16: 66 percent / trimethylsilyl trifluoromethanesulfonate / diethyl ether / 7 h / 0 °C

17: 40 percent / Bu₄NF / tetrahydrofuran; acetonitrile / 3 h / Ambient temperature

18: 63 percent

19: 83 percent / Bu₄NF / 2 h

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; silver carbonate; lithium diisopropyl amide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; paraffin; tert-butyl alcohol; benzene;

Reference yield:

2-benzyloxy-4-methoxy-1-(2-methoxyethoxy)benzene → 2α-(2,6-dimethoxyphenoxy)-6α-<4-(trans-3,7-dimethyl-2,6-octadienoxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane (142206-72-2)

Guidance literature:

Multi-step reaction with 18 steps

1: 83 percent / POCl₃ / 1 h / 60 °C

2: 47 percent / i-Pr₂NLi / tetrahydrofuran / 2 h / -75 °C

3: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

4: 67 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

5: 1) 2percent aq. OsO₄, N-methylmorpholine N-oxide, 2) NaIO₄ / 1) acetone, t-BuOH, r.t., 16 h, 2) EtOAc, H₂O, r.t., 2 h

6: 93 percent / Ag₂CO₃, celite / benzene / 0.5 h / Heating

7: 1) Et₃N, MeSO₂Cl, 2) Et₃N / 1) benzene, r.t., 2 h, 2) benzene, r.t., 16 h

8: 98 percent / N-methylmorpholine N-oxide, 2percent aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / Ambient temperature

9: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

10: 57 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

11: 82 percent / H₂ / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

12: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

13: 69 percent / DIBAL-H / toluene / 0.5 h / -75 °C

14: 74 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

15: 66 percent / trimethylsilyl trifluoromethanesulfonate / diethyl ether / 7 h / 0 °C

16: 40 percent / Bu₄NF / tetrahydrofuran; acetonitrile / 3 h / Ambient temperature

17: 63 percent

18: 83 percent / Bu₄NF / 2 h

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; silver carbonate; lithium diisopropyl amide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;

Reference yield:

4-benzyloxy-2-methoxy-5-(2-methoxyethoxy)benzaldehyde (142206-56-2) → 2α-(2,6-dimethoxyphenoxy)-6α-<4-(trans-3,7-dimethyl-2,6-octadienoxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane (142206-72-2)

Guidance literature:

Multi-step reaction with 17 steps

1: 47 percent / i-Pr₂NLi / tetrahydrofuran / 2 h / -75 °C

2: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

3: 67 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

4: 1) 2percent aq. OsO₄, N-methylmorpholine N-oxide, 2) NaIO₄ / 1) acetone, t-BuOH, r.t., 16 h, 2) EtOAc, H₂O, r.t., 2 h

5: 93 percent / Ag₂CO₃, celite / benzene / 0.5 h / Heating

6: 1) Et₃N, MeSO₂Cl, 2) Et₃N / 1) benzene, r.t., 2 h, 2) benzene, r.t., 16 h

7: 98 percent / N-methylmorpholine N-oxide, 2percent aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / Ambient temperature

8: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

9: 57 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

10: 82 percent / H₂ / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

11: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

12: 69 percent / DIBAL-H / toluene / 0.5 h / -75 °C

13: 74 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

14: 66 percent / trimethylsilyl trifluoromethanesulfonate / diethyl ether / 7 h / 0 °C

15: 40 percent / Bu₄NF / tetrahydrofuran; acetonitrile / 3 h / Ambient temperature

16: 63 percent

17: 83 percent / Bu₄NF / 2 h

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; silver carbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;

upstream raw materials:

3-benzyloxy-4-(2-methoxyethoxy)phenol

4-benzyloxy-2-methoxy-5-(2-methoxyethoxy)benzaldehyde

1α-hydroxy-6α-<4-hydroxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2-oxo-3,7-dioxabicyclo<3.3.0>octane

6α-<4-benzyloxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-1α-hydroxy-2-oxo-3,7-dioxabicyclo<3.3.0>octane

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