5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin

Base Information

Chemical Name:5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin
CAS No.:919365-40-5
Molecular Formula:C₇₄H₆₄O₁₀
Molecular Weight:1113.32
Hs Code.:

Synonyms:5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin

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Chemical Property of 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin

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Technology Process of 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin

There total 9 articles about 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin 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: 67.0%

: 919365-38-1
5,7,3',4'-tetra-O-benzyl-8-allyl-epicatechin

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

: 919365-40-5
5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 24h;
DOI:10.1021/jo061740e

Reference yield:

: 919365-35-8
5,7,3',4'-tetra-O-benzyl-8-bromo-3-(tert-butyldimethylsilyl)-catechin

: 919365-40-5
5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin

Guidance literature:: Multi-step reaction with 5 steps

1.1: 42 percent / nBuLi / tetrahydrofuran / 1 h / -78 °C

2.1: 83 percent / aq. HF / acetonitrile

3.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂; H₂O / 20 °C

4.1: lithium bromide; L-selectride / tetrahydrofuran / 2.25 h / -78 °C

4.2: 72 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol

5.1: 67 percent / DCC; DMAP / CH₂Cl₂ / 24 h

With dmap; n-butyllithium; hydrogen fluoride; L-Selectride; Dess-Martin periodane; dicyclohexyl-carbodiimide; lithium bromide; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo061740e

Reference yield:

: 919365-55-2
(R)-8-Allyl-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-one

: 919365-40-5
5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium bromide; L-selectride / tetrahydrofuran / 2.25 h / -78 °C

1.2: 72 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol

2.1: 67 percent / DCC; DMAP / CH₂Cl₂ / 24 h

With dmap; L-Selectride; dicyclohexyl-carbodiimide; lithium bromide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo061740e