(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate

Base Information

• Chemical Name: (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate
• CAS No.: 901125-29-9
• Molecular Formula: C₆₅H₅₆O₁₀
• Molecular Weight: 997.154

Synonyms:(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate

Chemical Property of (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate

Chemical Property:

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Technology Process of (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate

There total 2 articles about (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate 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:

3,5-bis(benzyloxy)-4-methoxybenzoyl chloride (19859-89-3) + 5,7,3',4'-tetra-O-benzylepicatechin (87292-49-7) → (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate (901125-29-9)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tet.2006.04.010

Reference yield:

[3,5-bis(benzyloxy)-4-methoxyphenyl]methanol (19859-90-6) → (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate (901125-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMF / CH₂Cl₂ / 3 h / Heating

2: DMAP / CH₂Cl₂ / 20 °C

With dmap; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1016/j.tet.2006.04.010

Reference yield: 88.0%

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate (901125-29-9) → (-)-(2R,3R)-5,7-dihydroxy-2-(3',4'-dihydroxy-phenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate (108907-44-4)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2006.04.010

upstream raw materials:

3,5-bis(benzyloxy)-4-methoxybenzoyl chloride

5,7,3',4'-tetra-O-benzylepicatechin

[3,5-bis(benzyloxy)-4-methoxyphenyl]methanol

Downstream raw materials:

(-)-(2R,3R)-5,7-dihydroxy-2-(3',4'-dihydroxy-phenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate

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