(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Base Information

Chemical Name:(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate
CAS No.:732298-13-4
Molecular Formula:C₇₁H₆₀O₁₀
Molecular Weight:1073.25
Hs Code.:

Synonyms:(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

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Chemical Property of (+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

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Technology Process of (+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

There total 11 articles about (+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate 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: 100.0%

: 1486-48-2
3,4,5-tribenzyloxybenzoic acid

: 20728-73-8
5,7,3',4'-tetra-O-benzyl-(+)-catechin

: 732298-13-4
(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2004.10.048

Reference yield:

: 1486-47-1
3,4,5-tris(benzyloxy)benzoyl chloride

: 20728-73-8
5,7,3',4'-tetra-O-benzyl-(+)-catechin

: 732298-13-4
(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Guidance literature:: With dmap; In dichloromethane; at 20 ℃;
DOI:10.1016/j.bmc.2004.04.033

Reference yield:

: 5447-02-9
3,4-dibenzyloxybenzaldehyde

: 732298-13-4
(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran; various solvent(s) / 2 h / 20 °C

2.1: 7.9 g / DIBAL / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

3.1: 47.3 percent / silica gel supported H₂SO₄ / CH₂Cl₂ / 20 °C

4.1: imidazole / dimethylformamide / 20 °C

5.1: AD-mixα; methanesulfonamide / H2O; 2-methyl-propan-2-ol; CH2Cl2 / 0 °C

6.1: TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: triethyl orthoformate; pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 5 h / 60 °C

7.2: K₂CO₃ / methanol; 1,2-dimethoxy-ethane / 20 °C

8.1: DMAP / CH₂Cl₂ / 20 °C

With 1H-imidazole; dmap; AD-mix-α; methanesulfonamide; sulfuric acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; sodium hydride; diisobutylaluminium hydride; orthoformic acid triethyl ester; In tetrahydrofuran; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Friedel-Craft alkylation / 5.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.bmc.2004.04.033