((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone

Base Information

• Chemical Name: ((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone
• CAS No.: 1453207-47-0
• Molecular Formula: C₄₃H₄₀O₁₀
• Molecular Weight: 716.785
• Mol file: 1453207-47-0.mol

Synonyms:((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone

Chemical Property of ((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone

There total 16 articles about ((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone 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:

C43H41IO10 → ((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone (1453207-47-0)

Guidance literature:

With palladium diacetate; triphenylphosphine; silver carbonate; In acetonitrile; at 115 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ol4021095

Reference yield:

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) → ((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone (1453207-47-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: potassium carbonate / acetone / 10 h / 80 °C

3.1: hydrogenchloride; water / methanol / 12 h / 30 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

4.2: Claisen-Schmidt Condensation / 12.67 h / 2 - 20 °C

5.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.55 h / 0 °C

5.2: 0.33 h / 20 °C

5.3: 0.75 h / -10 °C

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

7.1: hydroquinidein 1,4-phthalazinediyl diether; methanesulfonamide / tert-butyl alcohol; water / 0 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

9.1: pyridinium p-toluenesulfonate; orthoformic acid triethyl ester / 1,2-dichloro-ethane / 5.33 h / 20 - 50 °C

9.2: 20 °C

10.1: N-iodo-succinimide / N,N-dimethyl-formamide / 0 °C

11.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 20 °C

12.1: hydrogenchloride; water / methanol / 3 h / 50 °C

13.1: potassium phosphate / acetonitrile / 75 °C

14.1: palladium diacetate; triphenylphosphine; silver carbonate / acetonitrile / 15 h / 115 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; potassium phosphate; N-iodo-succinimide; methanesulfonamide; tetrabutyl ammonium fluoride; water; palladium diacetate; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; sodium hydride; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; triphenylphosphine; silver carbonate; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil; tert-butyl alcohol; 4.1: |Claisen-Schmidt Condensation / 7.1: |Sharpless Dihydroxylation / 14.1: |Heck Reaction;

DOI:10.1021/ol4021095

Reference yield:

1-(2-hydroxy-6-methoxy-4-(methoxymethoxy)phenyl)ethanone (404597-93-9) → ((2R,3S)-3-(benzyloxy)-5-methoxy-2,8-bis(4-methoxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl)(2,4,6-trimethoxyphenyl)methanone (1453207-47-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

1.2: Claisen-Schmidt Condensation / 12.67 h / 2 - 20 °C

2.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.55 h / 0 °C

2.2: 0.33 h / 20 °C

2.3: 0.75 h / -10 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

4.1: hydroquinidein 1,4-phthalazinediyl diether; methanesulfonamide / tert-butyl alcohol; water / 0 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

6.1: pyridinium p-toluenesulfonate; orthoformic acid triethyl ester / 1,2-dichloro-ethane / 5.33 h / 20 - 50 °C

6.2: 20 °C

7.1: N-iodo-succinimide / N,N-dimethyl-formamide / 0 °C

8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 20 °C

9.1: hydrogenchloride; water / methanol / 3 h / 50 °C

10.1: potassium phosphate / acetonitrile / 75 °C

11.1: palladium diacetate; triphenylphosphine; silver carbonate / acetonitrile / 15 h / 115 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; potassium phosphate; N-iodo-succinimide; methanesulfonamide; tetrabutyl ammonium fluoride; water; palladium diacetate; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; sodium hydride; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; orthoformic acid triethyl ester; triphenylphosphine; silver carbonate; In tetrahydrofuran; methanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; mineral oil; tert-butyl alcohol; 1.1: |Claisen-Schmidt Condensation / 4.1: |Sharpless Dihydroxylation / 11.1: |Heck Reaction;

DOI:10.1021/ol4021095

upstream raw materials:

(E)-tert-butyl(3-methoxy-5-(methoxymethoxy)-2-(3-(4-methoxyphenyl)allyl)phenoxy)dimethylsilane

(2R,3S)-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman-3-ol

(2R,3S)-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman-3-ol

(2R,3S)-3-(benzyloxy)-8-iodo-5-methoxy-7-(methoxymethoxy)-2-(4-methoxyphenyl)chroman

Downstream raw materials:

daphnodorin B