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

Base Information

• Chemical Name: 6α-<4-(4-chlorobenzyloxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-2β-(2,6-dimethoxyphenoxy)-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane
• CAS No.: 142206-68-6
• Molecular Formula: C₃₁H₃₅ClO₁₀
• Molecular Weight: 603.066

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 53 articles about 6α-<4-(4-chlorobenzyloxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-2β-(2,6-dimethoxyphenoxy)-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:

2-benzyloxy-4-methoxy-1-(2-methoxyethoxy)benzene → 6α-<4-(4-chlorobenzyloxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α-(2,6-dimethoxyphenoxy)-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane (142206-68-6,142236-83-7)

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: 68 percent

18: 51 percent / Bu₄NF / 16 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:

2-benzyloxy-4-methoxy-1-(2-methoxyethoxy)benzene → 6α-<4-(4-chlorobenzyloxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-2β-(2,6-dimethoxyphenoxy)-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane (142206-68-6,142236-83-7)

Guidance literature:

Multi-step reaction with 17 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: 17 percent / Bu₄NF / tetrahydrofuran; acetonitrile / 3 h / Ambient temperature

17: 60 percent

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:

3-(benzyloxy)-4-(2-methoxyethoxy)benzaldehyde → 6α-<4-(4-chlorobenzyloxy)-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α-(2,6-dimethoxyphenoxy)-1α-hydroxy-3,7-dioxabicyclo<3.3.0>octane (142206-68-6,142236-83-7)

Guidance literature:

Multi-step reaction with 20 steps

1: 1) m-chloroperbenzoic acid, KF, 2) NaOH / 1) CH₂Cl₂, r.t., 4 h, 2) CH₂Cl₂, H₂O, r.t., 30 min

2: 99 percent / NaH / tetrahydrofuran; paraffin / 48 h / Ambient temperature

3: 83 percent / POCl₃ / 1 h / 60 °C

4: 47 percent / i-Pr₂NLi / tetrahydrofuran / 2 h / -75 °C

5: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

6: 67 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

7: 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

8: 93 percent / Ag₂CO₃, celite / benzene / 0.5 h / Heating

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

10: 98 percent / N-methylmorpholine N-oxide, 2percent aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / Ambient temperature

11: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

12: 57 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

13: 82 percent / H₂ / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

14: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

15: 69 percent / DIBAL-H / toluene / 0.5 h / -75 °C

16: 74 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

17: 66 percent / trimethylsilyl trifluoromethanesulfonate / diethyl ether / 7 h / 0 °C

18: 40 percent / Bu₄NF / tetrahydrofuran; acetonitrile / 3 h / Ambient temperature

19: 68 percent

20: 51 percent / Bu₄NF / 16 h

With 2,6-dimethylpyridine; potassium fluoride; sodium hydroxide; 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; 3-chloro-benzenecarboperoxoic acid; 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;

upstream raw materials:

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

1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-hydroxy-3,7-dioxabicyclo<3.3.0>octane

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