(2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol

Base Information

• Chemical Name: (2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol
• CAS No.: 1607010-87-6
• Molecular Formula: C₄₃H₃₈O₆
• Molecular Weight: 650.771
• Mol file: 1607010-87-6.mol

Synonyms:(2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol

Chemical Property of (2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol

There total 6 articles about (2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol 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: 42.0%

(S)-2-(R)-(3,5-bis(benzyloxy)-phenyl)-(3,5-dibenzyloxyphenoxy)-methyl oxirane (1607010-84-3) → (2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol (1607010-87-6)

Guidance literature:

With 1,1,1,3',3',3'-hexafluoro-propanol; Sealed tube; Heating;

DOI:10.1016/j.tet.2014.03.052

Reference yield:

3-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-1-(3,5-bis(benzyloxy)phenyl)propane-1,2-diol → (2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol (1607010-87-6) + (2S,3R)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol

Guidance literature:

With pyridinium p-toluenesulfonate; orthoformic acid triethyl ester; In 1,2-dichloro-ethane; at 20 - 55 ℃; for 5.33h; Overall yield = 65 percent; Overall yield = 1.0 g;

DOI:10.14233/ajchem.2019.22064

Reference yield:

(2S,3R)-3-(3,5-dibenzyloxyphenoxy)-3-(3,5-dibenzyloxyphenyl)-propane-1,2-diol (1607010-81-0) → (2R,3S)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)-3,4-dihydro-2H-1-benzopyran-3-ol (1607010-87-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 48 h / 20 °C

1.2: 2 h / 20 °C

2.1: 1,1,1,3',3',3'-hexafluoro-propanol / Sealed tube; Heating

With dmap; 1,1,1,3',3',3'-hexafluoro-propanol; triethylamine; p-toluenesulfonyl chloride; In dichloromethane;

DOI:10.1016/j.tet.2014.03.052

upstream raw materials:

(2S,3R)-3-(3,5-dibenzyloxyphenoxy)-3-(3,5-dibenzyloxyphenyl)-propane-1,2-diol

(S)-2-(R)-(3,5-bis(benzyloxy)-phenyl)-(3,5-dibenzyloxyphenoxy)-methyl oxirane

(2S,3S)-3-(3,5-bis(benzyloxy)-phenyl)-oxiran-2-yl methanol

Downstream raw materials:

(R)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)chroman-3-one

(2R,3R)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)chroman-3-ol