(+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one

Base Information

Chemical Name:(+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one
CAS No.:901125-39-1
Molecular Formula:C₄₄H₃₈O₇
Molecular Weight:678.782
Hs Code.:

Synonyms:(+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one

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Chemical Property of (+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one

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Technology Process of (+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one

There total 9 articles about (+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one 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: 85.7%

: 901125-38-0
(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-ol

: 901125-39-1
(+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2006.04.010

Reference yield:

: 901125-35-7
(E)-3,5-bis(benzyloxy)-4-methoxycinnamyl alcohol

: 901125-39-1
(+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 45.1 percent / H₂SO₄/SiO₂ / CH₂Cl₂ / 20 °C

2.1: imidazole / dimethylformamide / 20 °C

3.1: AD-mix α; methanesulfonamide / CH2Cl2; 2-methyl-propan-2-ol; H2O / 0 °C

4.1: 2.2 g / TBAF / tetrahydrofuran / 4 h / 20 °C

5.1: triethyl orthoformate; PPTS / 5 h / 50 °C

5.2: 71.8 percent / K₂CO₃ / 1,2-dimethoxy-ethane; methanol / 20 °C

6.1: 85.7 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; AD-mix-α; methanesulfonamide; sulfuric acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; Dess-Martin periodane; orthoformic acid triethyl ester; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.04.010

Reference yield:

: 901125-34-6
ethyl (E)-3,5-bis(benzyloxy)-4-methoxycinnamate

: 901125-39-1
(+)-(2R)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 91 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

2.1: 45.1 percent / H₂SO₄/SiO₂ / CH₂Cl₂ / 20 °C

3.1: imidazole / dimethylformamide / 20 °C

4.1: AD-mix α; methanesulfonamide / CH2Cl2; 2-methyl-propan-2-ol; H2O / 0 °C

5.1: 2.2 g / TBAF / tetrahydrofuran / 4 h / 20 °C

6.1: triethyl orthoformate; PPTS / 5 h / 50 °C

6.2: 71.8 percent / K₂CO₃ / 1,2-dimethoxy-ethane; methanol / 20 °C

7.1: 85.7 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; AD-mix-α; methanesulfonamide; sulfuric acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; diisobutylaluminium hydride; Dess-Martin periodane; orthoformic acid triethyl ester; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.04.010