(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

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Chemical Name:(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate
CAS No.:773859-60-2
Molecular Formula:C₆₄H₅₄O₉
Molecular Weight:967.127
Hs Code.:

Synonyms:(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

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Chemical Property of (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

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Technology Process of (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

There total 9 articles about (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)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: 96.0%

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

: 773859-58-8
(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-ol

: 773859-60-2
(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1039/c003464a

Reference yield: 82.0%

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

: 773859-58-8
(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-ol

: 773859-60-2
(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Guidance literature:: With dmap; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.tet.2004.06.113

Reference yield:

: 63604-98-8
1,3-dibenzylphloroglucinol

: 773859-60-2
(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 38 percent / H₂SO₄; SiO₂ / H₂O; CH₂Cl₂ / 20 °C

2.1: imidazole / dimethylformamide / 20 °C

3.1: AD-mixα; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O; CH2Cl2 / 0 °C

4.1: 1.3 g / TBAF / tetrahydrofuran / 4 h / 20 °C

5.1: CH(OEt)3; PPTS / 1,2-dichloro-ethane / 5 h / 20 - 60 °C

5.2: 75 percent / K₂CO₃ / methanol; 1,2-dimethoxy-ethane / 20 °C

6.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7.1: 71 percent / L-selectride / tetrahydrofuran / -78 °C

8.1: 82 percent / DMAP / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; dmap; AD-mix-α; methanesulfonamide; sulfuric acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; L-Selectride; Dess-Martin periodane; orthoformic acid triethyl ester; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Friedel-Craft alkylation reaction / 3.1: Sharless hydroxylation;
DOI:10.1016/j.tet.2004.06.113